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【结 构 式】

【分子编号】11291

【品名】Dihydro-2,5-furandione; Succinic anhydride

【CA登记号】108-30-5

【 分 子 式 】C4H4O3

【 分 子 量 】100.07396

【元素组成】C 48.01% H 4.03% O 47.96%
与该中间体有关的原料药合成路线共 30 条
合成路线1合成路线2合成路线3合成路线4合成路线5合成路线6合成路线7合成路线8合成路线9合成路线10合成路线11合成路线12合成路线13合成路线14合成路线15合成路线16合成路线17合成路线18合成路线19合成路线20合成路线21合成路线22合成路线23合成路线24合成路线25合成路线26合成路线27合成路线28合成路线29合成路线30

合成路线1

该中间体在本合成路线中的序号：(V)

The oxidation of 3-beta-acetoxyolean-12-en-30-oic acid methyl ester (I) with H2O2 in hot acetic acid gives 3beta-acetoxy-12-oxoolean-30-oic acid methyl ester (II), which is treated with Br2 in 40% HBr acetic acid yielding 3beta-acetoxy-12-oxoolean 9-en-30-oic acid methyl ester (III). The reduction of (III) with hydrazine and sodium ethoxide in ethanol affords 3beta-hydroxyolean-9(11)-en-30-oic acid (IV), which is finally esterified with succinic anhydride (V) in hot pyridine.

参考文献 中间体
合成目标
【1】 Pifferi, G.; Umani Ronchi, A.; Farina, C.; Gamba, A. (ISF SpA); 3beta-Hydroxy-18beta-olean-9-en-30-oic acids. DE 2811253; FR 2383909; GB 1575494; JP 78116363; US 4173648 .
【2】 Prous, J.; Castaner, J.; Deloxolone sodium. Drugs Fut 1986, 11, 8, 643.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 23967 (2S,4aS,6aR,6bR,8aR,10S,12aR,14bR)-10-(acetoxy)-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydro-2-picenyl acetate C33H52O4 详情 详情
(II) 23980 (2S,4aS,6aR,6bR,8aR,10S,12aR,14aR,14bS)-10-(acetoxy)-2,4a,6a,6b,9,9,12a-heptamethyl-14-oxodocosahydro-2-picenyl acetate C33H52O5 详情 详情
(III) 23968 (2S,4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-(acetoxy)-2,4a,6a,6b,9,9,12a-heptamethyl-14-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-2-picenyl acetate C33H50O5 详情 详情
(IV) 23969 (2S,4aS,6aR,6bS,8aR,10S,12aS,14aR,14bS)-10-hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydro-2-picenecarboxylic acid C30H48O3 详情 详情
(V) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线2

该中间体在本合成路线中的序号：(II)

The condensation of benzoin (I) with succinic anhydride (II) by heating at 120 C gives benzoin hemisuccinate (III), which is cyclized with ammonium acetate in refluxing acetic acid.

参考文献 中间体
合成目标
【1】 Brown, K. (Wyeth-Ayerst Laboratories); Oxazoles. GB 1206403; YU 244367; YU 249673 .
【2】 Brown, K. (Wyeth-Ayerst Laboratories); Oxazoles. US 3578671 .
【3】 Arrigoni-Martelli, E.; Castaner, J.; Oxaprozin. Drugs Fut 1978, 3, 7, 539.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 24135 2-hydroxy-1,2-diphenyl-1-ethanone; benzoin 579-44-2 C14H12O2 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 33528 4-oxo-4-(2-oxo-1,2-diphenylethoxy)butyric acid C18H16O5 详情 详情

合成路线3

该中间体在本合成路线中的序号：(B)

The esterification of 4-phenoxy-3-nitro-5-sulfamoylbenzoic acid (I) with methanol and H2SO4 gives the corresponding methyl ester (II), which is reduced with H2 over Raney-Ni in methanol yielding methyl 4-phenoxy-3-amino-5-sulfamoylbenzoate (III). The condensation of (III) with succinic anhydride (B) or succinoyl chloride (A) by means of pyridine in refluxing dioxane affords methyl 4-phenoxy-3N-succinimido-5-sulfamoylbenzoate (IV), which is reduced with borontrifluoride ethearate and NaBH4 in diglyme giving methyl 4-phenoxy-3-(1-pyrrolidinyl)-5-sulfamoylbenzoate (V). Finally, this compound is hydrolyzed with NaOH in water.

参考文献 中间体
合成目标
【1】 Merkel, W.; et al.; Piretanide (Hoe 118) a new high ceiling salidiuretic. Eur J Med Chem 1976, 11, 5, 399.
【2】 Bormann, D.; et al.; 5-Sulfamoylbenzoic acid derivatives carrying a heterocyclic substituent. DE 2419970; FR 2324298; GB 1504505; US 4010273 .
【3】 Hillier, K.; Castaner, J.; Piretanide. Drugs Fut 1977, 2, 6, 393.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(A) 33879 succinoyl dichloride 543-20-4 C4H4Cl2O2 详情 详情
(I) 33876 3-(aminosulfonyl)-5-nitro-4-phenoxybenzoic acid C13H10N2O7S 详情 详情
(II) 33877 methyl 3-(aminosulfonyl)-5-nitro-4-phenoxybenzoate C14H12N2O7S 详情 详情
(III) 33878 methyl 3-amino-5-(aminosulfonyl)-4-phenoxybenzoate C14H14N2O5S 详情 详情
(IV) 33880 methyl 3-(aminosulfonyl)-5-(2,5-dioxo-1-pyrrolidinyl)-4-phenoxybenzoate C18H16N2O7S 详情 详情
(V) 33881 methyl 3-(aminosulfonyl)-4-phenoxy-5-(1-pyrrolidinyl)benzoate C18H20N2O5S 详情 详情

合成路线4

该中间体在本合成路线中的序号：(II)

By acylation of 1-ethyl-6-fluoro-4-oxo-7-piperazine-1,4-dihydroquinoline-3-carboxylic acid (I) with succinic anhydride (II) in refluxing dichloromethane. Acetic acid can also be used as solvent in the acylation.

参考文献 中间体
合成目标
【1】 Di Schiena, M. (Farmades); Cpds. having antibacterial activity, process for their preparation and pharmaceutical compsns. Containing them. EP 0155006 .
【2】 Prous, J.; Castaner, J.; NORFLOXACIN SUCCINIL. Drugs Fut 1990, 15, 6, 578.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11290 1-Ethyl-6-fluoro-4-oxo-7-piperazino-1,4-dihydro-3-quinolinecarboxylic acid; Norfloxacin 70458-96-7 C16H18FN3O3 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线5

该中间体在本合成路线中的序号：(A)

Rearrangement of 2-methylpropanoic acid, 2-phenylhydrazide (I) provides 1,3-dihydro-3,3-dimethyl-2H-indol-2-one (II). Friedel Crafts' acylation of (II) with succinic anhydride in an aluminum chloride/DMF melt results in the formation of 4-oxobutanoic acid (III). Cyclization of (III) with hydrazine in refluxing ethanol completes the preparation of LY-195115.

参考文献 中间体
合成目标
【1】 Hayes, J.S.; Robertson, D.W.; LY-195115 . Drugs Fut 1986, 11, 5, 377.
【2】 Robertson, D.W.; et al.; Dihydropyridazinone cardiotonics: The discovery and inotropic activity of 1,3-dihydro-3,3-dimethyl-5-(1,4,5,6-tetrahydro-6-oxo-3-pyridazinyl)-2H-indol-2-one. J Med Chem 1986, 29, 10, 1832-40.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(I) 24021 2-methyl-N'-phenylpropanohydrazide C10H14N2O 详情 详情
(II) 21599 3,3-dimethyl-1,3-dihydro-2H-indol-2-one C10H11NO 详情 详情
(III) 24024 4-(3,3-dimethyl-2-oxo-2,3-dihydro-1H-indol-5-yl)-4-oxobutyric acid C14H15NO4 详情 详情

合成路线6

该中间体在本合成路线中的序号：(B)

The reaction of 1-amino-5-nitropentane (I) with benzyloxycarbonyl chloride (A) by means of NaOH in water gives 1-carbobenzoxyamino-5-nitropentane (II), which by reduction with Zn and ammonium chloride in ethanol - water yields 1-carbobenzoxyamino-5-hydroxylaminopentane (III). The reaction of (III) with succinic anhydride (B) by means of NaOH in pyridine water affords 1-carbobenzoxyamino-5-(N-succinylhydroxylamino)pentane (IV), which is cyclized with hot acetic anhydride giving 2-(5-carbobenzoxyaminopentyl)-3,6-dioxotetrahydro-1,2-oxazine (V). The reaction of (V) with the nitroamine (I) by means of sodium methoxide in methanol yields 1-carbobenzoxy-6-hydroxy-16-nitro-7,10-dioxo-6,11-diazahexadecane (VI), which is reduced with Zn and acetylated as before affording 1-carboxybenzoxyamino-6-hydroxy-16-(N-acetylhydroxylamino)-7,10-dioxo-6,11-diazahexadecane (VII).

参考文献 中间体
合成目标
【1】 Prelog, V.; Walser, A.; 75. Stoffweschselprodukte con actinomyceten. Uber die synthese der ferrioxamine B und D1. Helv Chim Acta 1962, 45, 631-637.
【2】 Bickel, H.; et al.; 153. Stoffweschselprodukte von mikroorganismen. Zur henntnis von desferrioxamin B. Helv Chim Acta 1963, 46, 1385-89.
【3】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Hopkins, S.J.; Liposome-Entrapped Desferrioxamine deferoxamine. Drugs Fut 1979, 4, 7, 500.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(A) 24261 1-[2-(chlorooxy)-2-oxoethyl]benzene C8H7ClO2 详情 详情
(I) 33387 5-nitropentylamine; 5-nitro-1-pentanamine C5H12N2O2 详情 详情
(II) 33388 benzyl 5-nitropentylcarbamate C13H18N2O4 详情 详情
(III) 33389 benzyl 5-(hydroxyamino)pentylcarbamate C13H20N2O3 详情 详情
(IV) 33390 4-[(5-[[(benzyloxy)carbonyl]amino]pentyl)(hydroxy)amino]-4-oxobutyric acid C17H24N2O6 详情 详情
(V) 33391 benzyl 5-(3,6-dioxo-1,2-oxazinan-2-yl)pentylcarbamate C17H22N2O5 详情 详情
(VI) 33392 benzyl 5-(hydroxy[4-[(5-nitropentyl)amino]-4-oxobutanoyl]amino)pentylcarbamate C22H34N4O7 详情 详情
(VII) 33393 benzyl 5-[[4-([5-[acetyl(hydroxy)amino]pentyl]amino)-4-oxobutanoyl](hydroxy)amino]pentylcarbamate C24H38N4O7 详情 详情

合成路线7

该中间体在本合成路线中的序号：(II)

A new synthesis of tepoxalin has been described: The condensation of 4-chloroacetophenone (I) with succinic anhydride (II) by means of lithium bis(trimethylsilyl)amide in THF at -20 C gives 6-(4-chlorophenyl)-4,6-dioxohexanoic acid (III), which is cyclized with 4-methoxyphenylhydrazine (IV) by means of triethylamine in methanol at room temperature to afford 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)pyrazol-3-yl]propanoic acid (V); finally this compound is condensed with methylhydroxylamine (VI) by means of oxalyl chloride and triethylamine at room temperature.

参考文献 中间体
合成目标
【1】 Forerokelly, Y.; Murray, W.; Wachter, M.; Barton, D.; The regioselective synthesis of tepoxalin, 3-[5-(4-chlorophenyl)-1-(4-methoxyphenyl)-3-pyrazolyl]-N-hydroxy-N-methylpropanamide and related 1,5-diarylpyrazole antiinflammatory agents. Synthesis 1991, 1, 1, 18.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 12685 4-Chloroacetophenone; 1-(4-Chlorophenyl)-1-ethanone; p-Chloroacetophenone 99-91-2 C8H7ClO 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 12687 6-(4-Chlorophenyl)-4,6-dioxohexanoic acid C12H11ClO4 详情 详情
(IV) 12688 4-Hydrazinophenyl methyl ether; 1-(4-Methoxyphenyl)hydrazine 3471-32-7 C7H10N2O 详情 详情
(V) 12689 3-[5-(4-Chlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-yl]propionic acid C19H17ClN2O3 详情 详情
(VI) 12690 (Hydroxyamino)methane; N-Methylhydroxylamine 593-77-1 CH5NO 详情 详情

合成路线8

该中间体在本合成路线中的序号：(II)

A new synthesis of roxindole has been described: The condensation of 5-methoxyindole (I) with succinic anhydride (II) by means of methylmagnesium bromide in hot anisole gives the 4-oxobutyric acid derivative (III), which is condensed with the 4-phenyltetrahydropyridine (IV) by means of EDC and DIPEA in DMF yielding the butanedione (V). The reduction of (V) with LiAlH4 in refluxing THF affords intermediate (VI), which is finally demethylated with DIBAH in refluxing toluene.

参考文献 中间体
合成目标
【1】 Lange, J.H.M.; et al.; A straightforward synthetic approach for roxindole. Bioorg Med Chem Lett 1999, 9, 7, 1055.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 25902 1H-Indol-5-yl methyl ether; 5-Methoxy-1H-indole; 5-Methoxyindole 1006-94-6 C9H9NO 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 30614 4-(5-methoxy-1H-indol-3-yl)-4-oxobutyric acid C13H13NO4 详情 详情
(IV) 13002 4-Phenyl-1,2,3,6-tetrahydropyridine; 1,2,3,6-Tetrahydro-4-phenyl-pyridine 10338-69-9 C11H13N 详情 详情
(V) 30615 1-(5-methoxy-1H-indol-3-yl)-4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]-1,4-butanedione C24H24N2O3 详情 详情
(VI) 12999 5-Methoxy-3-[4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-indole; Methyl 3-[4-[4-phenyl-3,6-dihydro-1(2H)-pyridinyl]butyl]-1H-indol-5-yl ether C24H28N2O 详情 详情

合成路线9

该中间体在本合成路线中的序号：(V)

The reaction of 2-hydroxy-3'-methoxybibenzyl (I) with epichlorohydrin (II) by means of NaH in DMF gives 2-(2,3-epoxypropoxy)-3'-methoxybibenzyl (III), which by reaction with dimethylamine in refluxing THF yields 2-[3-(dimethylamino)-2-hydroxypropoxy]-3'-methoxybibenzyl (IV). Finally, this compound is treated with succinic anhydride (V) in refluxing THF and with HCl in acetone.

参考文献 中间体
合成目标
【1】 Kikumoto, R.; Fukami, H.; Hara, H.; Ninomiya, K.; Sugano, M. (Mitsubishi Chemical Corp.); Pharmaceutically active (3-aminopropoxy)-bibenzyl derivs. EP 0072942 .
【2】 Prous, J.; Castaner, J.; Sarpogrelate Hydrochloride. Drugs Fut 1992, 17, 12, 1093.
【3】 Osakabe, M.; Fukami, H.; Sugano, M.; Kikumoto, R.; Ninomiya, K.; Tamao, Y.; Hara, H.; Syntheses and platelet aggregation inhibitory and antithrombotic properties of [2-[(omega-aminoalkoxy)phenyl]ethyl]benzenes. J Med Chem 1990, 33, 6, 1818.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(II) 13604 2-(3-Methoxyphenethyl)phenol C15H16O2 详情 详情
(III) 13605 2-(3-Methoxyphenethyl)phenyl 2-oxiranylmethyl ether; 2-[[2-(3-Methoxyphenethyl)phenoxy]methyl]oxirane C18H20O3 详情 详情
(IV) 13606 1-(Dimethylamino)-3-[2-(3-methoxyphenethyl)phenoxy]-2-propanol C20H27NO3 详情 详情
(V) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线10

该中间体在本合成路线中的序号：(XIV)

The esterification of pyridine-2,5-dicarboxylic acid (I) with thionyl chloride/methanol gives the corresponding dimethyl ester (II), which is hydrogenated with H2 over PtO2 in acetic acid yielding piperidine-2,5-dicarboxylic acid dimethyl ester (III), as a mixture of the cis- and trans-isomers. The condensation of (III) with 2-chloroacetonitrile (IV) by means of Na2CO3 in refluxing isobutyl methyl ketone affords the expected 1-(cyanomethyl) derivative (V), which is cyclized by hydrogenation with H2 over RaNi in methanol/ethyl acetate giving racemic cis-1-oxo-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine-7-carboxylic acid methyl ester (VI). The reduction of (VI) with LiAlH4 in refluxing THF yields the corresponding hydroxymethyl derivative (VII), which is condensed with 2-chloropyrimidine by means of Na2CO3 in refluxing water affording racemic cis-7-(hydroxymethyl)-2-(2-pyrimidinyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (IX). The reaction of (IX) with methanesulfonyl chloride and triethylamine gives the expected mesylate (X), which is treated with sodium azide in DMF to afford the corresponding azido derivative (XI). The reaction of (XI) with hydrazine in refluxing ethanol gives the racemic cis-7-(aminomethyl)-2-(2-pyrimidinyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (XII), which is submitted to optical resolution by formation of the corresponding salt with (-)-mandelic acid, separation of the diastereomers by crystallization, and decomposition of the desired salt with NaOH to yield (7R,9aS)-7-(aminomethyl)-2-(2-pyrimidinyl)-2,3,4,6,7,8,9,9a-octahydro-1H-pyrido[1,2-a]pyrazine (XIII). Finally, this compound is condensed with succinic anhydride (XIV) in refluxing xylene.

参考文献 中间体
合成目标
【1】 Castaner, J.; Graul, J.; Silvestre, J.S.; Sunepitron Hydrochloride. Drugs Fut 1998, 23, 2, 161.
【2】 Desai, K.A.; Bright, G.M. (Pfizer Inc.); Bis-aza-bicyclic anxiolytic agents and antidepressants. EP 0380217; JP 1990233681; US 5122525; WO 9008144; WO 9008148 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 14440 2,5-pyridinedicarboxylic acid 100-26-5 C7H5NO4 详情 详情
(II) 14441 dimethyl 2,5-pyridinedicarboxylate 881-86-7 C9H9NO4 详情 详情
(III) 14442 dimethyl 2,5-piperidinedicarboxylate C9H15NO4 详情 详情
(IV) 14443 2-chloroacetonitrile; chloroacetonitrile 107-14-2 C2H2ClN 详情 详情
(V) 14444 dimethyl 1-(cyanomethyl)-2,5-piperidinedicarboxylate C11H16N2O4 详情 详情
(VI) 14445 methyl (7S,9aS)-1-oxooctahydro-2H-pyrido[1,2-a]pyrazine-7-carboxylate C10H16N2O3 详情 详情
(VII) 14446 (7S,9aS)octahydro-2H-pyrido[1,2-a]pyrazin-7-ylmethanol C9H18N2O 详情 详情
(VIII) 11191 2-Chloropyrimidine 1722-12-9 C4H3ClN2 详情 详情
(IX) 14448 [(7S,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methanol C13H20N4O 详情 详情
(X) 14449 [(7S,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methyl methanesulfonate C14H22N4O3S 详情 详情
(XI) 14450 [(7S,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methyl azide; (7S,9aS)-7-(azidomethyl)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazine C13H19N7 详情 详情
(XII) 63830 [(7S,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methylamine; [(7S,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methanamine C13H21N5 详情 详情
(XIII) 14451 [(7R,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methylamine; [(7R,9aS)-2-(2-pyrimidinyl)octahydro-2H-pyrido[1,2-a]pyrazin-7-yl]methanamine C13H21N5 详情 详情
(XIV) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线11

该中间体在本合成路线中的序号：(IV)

The acylation of aniline (I) with methanesulfonyl chloride (II) in pyridine gives the corresponding sulfonamide (III), which is submitted to a Friedel-Crafts condensation with succinic anhydride (IV) and AlCl3 in hot carbon disulfide to afford 4-[4-(methanesulfonyl)phenyl]-4-oxobutyric acid (V). The amidation of (V) with N-ethylheptylamine (VI) yields the corresponding amide (VII), which is finally reduced with LiAlH4 in THF and treated with an ethanolic solution of fumaric acid in order to precipitate the corresponding salt.

参考文献 中间体
合成目标
【1】 Stolle, W.T.; Stelzer, L.S.; Hester, J.B.; Perricone, S.C.; Hsi, R.S.P.; Synthesis of radiolabeled racemic and enantiomeric antiarrhythmic agents. J Label Compd Radiopharm 1994, 34, 10, 929.
【2】 Robinson, C.; Robinson, K.; Castaner, J.; Ibutilide Fumarate. Drugs Fut 1996, 21, 9, 894.
【3】 Hester, J.B. Jr. (Pharmacia Corp.); N-(Aminoalkylphenyl)sulfonamides their preparation and therapeutic use. EP 0164865; JP 1985239458; US 5155268 .
【4】 Hester, J.B.; Gibson, J.K.; Cimini, M.G.; Emmert, D.E.; Locker, P.K.; Perricone, S.C.; Skaletzky, L.L.; Sykes, J.K.; West, B.E.; N-[(omega-Amino-1-hydroxyalkyl)phenyl]methanesulfonamide derivatives with Class III antiarrhythmic activity. J Med Chem 1991, 34, 1, 308-15.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 12294 Aniline; Phenylamine 62-53-3 C6H7N 详情 详情
(II) 13467 Methanesulfonyl chloride;Mesyl chloride;Methylsulfonyl chloride;Methanesulfonic acid chloride;Methanesulfonyl chloride;Methanesulphonyl chloride 124-63-0 CH3ClO2S 详情 详情
(III) 13699 N-Phenylmethanesulfonamide; N-Phenyl methanesulfonamide 1197-22-4 C7H9NO2S 详情 详情
(IV) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(V) 14625 4-[4-[(methylsulfonyl)amino]phenyl]-4-oxobutyric acid C11H13NO5S 详情 详情
(VI) 14626 N-ethyl-1-heptanamine; N-ethyl-N-heptylamine C9H21N 详情 详情
(VII) 14627 N-ethyl-N-heptyl-4-[4-[(methylsulfonyl)amino]phenyl]-4-oxobutanamide C20H32N2O4S 详情 详情

合成路线12

该中间体在本合成路线中的序号：(XII)

Alternatively, the mono-methyl ester of succinic acid (XIII) was prepared by refluxing succinic anhydride (XII) with MeOH. Subsequent treatment of (XIII) with SOCl2 gave acid chloride (XIV). This was condensed with diazomethane to produce the diazo ketone (XV), which was further converted to the chloro ketone (XVI) by treatment with HCl. Condensation of chlorolevulinate (XVI) with succinimide (XVII) produced methyl delta-succinimidolevulinate (XVIII). Smooth acidic hydrolysis of the methyl ester group of (XVIII) led to the succinimido acid (XIX), which was further hydrolyzed to the succinamido acid (XX) under basic conditions. The title compound could be obtained by hydrolysis of either (XVIII), (XIX) or (XX) in refluxing 7N HCl.

参考文献 中间体
合成目标
【1】 Neuberger, A.; Scott, J.J.; The synhtesis of delta-succinamidolaevulic acid and related compounds. J Chem Soc 1954, 1820.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XII) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(XIII) 55901 Methyl hydrogen succinate; Succinic acid monomethyl ester; Monomethyl succinate 3878-55-5 C5H8O4 详情 详情
(XIV) 18060 4-Chloro-4-oxobutyric acid methyl ester; 3-Carbomethosypropionyl chloride; Methyl 4-chloro-4-oxobutanoate 1490-25-1 C5H7ClO3 详情 详情
(XV) 59148 　 C6H8N2O3 详情 详情
(XVI) 59149 methyl 5-chloro-4-oxopentanoate C6H9ClO3 详情 详情
(XVII) 22543 2,5-pyrrolidinedione 123-56-8 C4H5NO2 详情 详情
(XVIII) 59150 methyl 5-(2,5-dioxo-1-pyrrolidinyl)-4-oxopentanoate C10H13NO5 详情 详情
(XIX) 59151 5-(2,5-Dioxopyrrolidin-1-yl)-4-oxopentanoic acid C9H11NO5 详情 详情
(XX) 59152 5-[(3-carboxypropanoyl)amino]-4-oxopentanoic acid C9H13NO6 详情 详情

合成路线13

该中间体在本合成路线中的序号：(XII)

The acylation of hippuric acid (LXI) with methyl succinyl chloride (XIV) in cold 4-picoline gave rise to the acyl oxazolinone (LXII). Subsequent acidic hydrolysis of (LXII) provided delta-aminolevulinic acid. In a related strategy, the lithio-dianion of ethyl hippurate (LXIII) was acylated with succinic anhydride (XII) producing the 2-amino-3-oxoadipic acid derivative (LXIV). Further hydrolysis and decarboxylation of (LXIV) under acidic conditions furnished the target compound.

参考文献 中间体
合成目标
【1】 Sidebottom, P.J.; Evans, D.A.; A simple route to alpha-aminoketones and related derivatives by dianion acylation reactions; an improved preparation of delta-aminolevulinic acid. J Chem Soc Chem Commun 1978, 753.
【2】 Aronova, N.I.; Makhova, N.N.; Zavyalov, S.I.; Volkenshtein, J.B.; Kunitskaya, G.M.; Method of producing delta-aminolevulinic acid hydrochloride. US 3846490 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XII) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(XIV) 18060 4-Chloro-4-oxobutyric acid methyl ester; 3-Carbomethosypropionyl chloride; Methyl 4-chloro-4-oxobutanoate 1490-25-1 C5H7ClO3 详情 详情
(LXI) 27236 2-(benzoylamino)acetic acid 495-69-2 C9H9NO3 详情 详情
(LXII) 59186 methyl 4-oxo-4-(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-yl)butanoate C14H13NO5 详情 详情
(LXIII) 59187 Ethyl hippurate C11H13NO3 详情 详情
(LXIV) 59188 5-(benzoylamino)-6-ethoxy-4,6-dioxohexanoic acid C15H17NO6 详情 详情

合成路线14

该中间体在本合成路线中的序号：(II)

Friedel-Crafts acylation of 2-fluorotoluene (I) with succinic anhydride (II) in the presence of AlCl3 afforded 4-(4-fluoro-3-methylphenyl)-4-oxobutanoic acid (III). Ketone (III) reduction by hydrogenation over Pd/C furnished the arylbutyric acid (IV), which was esterified to (V) by means of SOCl2 in MeOH. Subsequent aromatic ring nitration of (V) yielded (VI). After basic hydrolysis of the methyl ester of (VI), the arylbutyric acid (VII) was subjected to intramolecular cyclization in hot polyphosphoric acid producing tetralone (VIII). Reduction of the keto group of (VIII) with NaBH4, followed by dehydration of the resultant alcohol (IX) under acidic conditions, gave rise to the dihydronaphthalene (X). Hydrogenation of the olefin double bond of (X) and simultaneous nitro group reduction in the presence of PtO2 produced the amino tetralin (XI). The amino group of (XI) was further protected as the acetamide (XII) employing Ac2O and Et3N. Regioselective benzylic oxidation of (XII) with KMnO4 gave tetralone (XIII). Functionalization of the alpha position of (XIII) to ketone was achieved employing n-butyl nitrite and potassium tert-butoxide. The resulting keto oxime (XIV) was then reduced with zinc in the presence of Ac2O, yielding acetamide (XV). Both amide functions of (XV) were hydrolyzed under acidic conditions to give diamine (XVI). The aliphatic amine of (XVI) was then selectively acylated with ethyl trifluoroacetate to produce the trifluoroacetamide (XVII).

参考文献 中间体
合成目标
【1】 Chilman-Blair, K.; Mealy, N.E.; Castaner, J.; Bayes, M.; Exatecan Mesilate. Drugs Fut 2004, 29, 1, 9.
【2】 Terasawa, H.; Ejima, A.; Ohsuki, S.; Uoto, K. (Daiichi Pharmaceutical Co., Ltd.; Yakult Honsha Co., Ltd.); Hexacyclic cpd.. EP 0495432; JP 1993059061; US 5834476; US 6407115 .
【3】 Terasawa, H.; Sato, K.; Mitsui, I. (Daiichi Pharmaceutical Co., Ltd.; Yakult Honsha Co., Ltd.); Antitumor agents. JP 1994087746 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 52759 2-Fluorotoluene; o-Fluorotoluene 95-52-3 C7H7F 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 52760 4-(4-fluoro-3-methylphenyl)-4-oxobutanoic acid C11H11FO3 详情 详情
(IV) 52761 4-(4-fluoro-3-methylphenyl)butanoic acid C11H13FO2 详情 详情
(V) 52762 methyl 4-(4-fluoro-3-methylphenyl)butanoate C12H15FO2 详情 详情
(VI) 52763 methyl 4-(4-fluoro-5-methyl-2-nitrophenyl)butanoate C12H14FNO4 详情 详情
(VII) 52764 4-(4-fluoro-5-methyl-2-nitrophenyl)butanoic acid C11H12FNO4 详情 详情
(VIII) 52765 7-fluoro-8-methyl-5-nitro-3,4-dihydro-1(2H)-naphthalenone C11H10FNO3 详情 详情
(IX) 52766 7-fluoro-8-methyl-5-nitro-1,2,3,4-tetrahydro-1-naphthalenol C11H12FNO3 详情 详情
(X) 52767 6-fluoro-5-methyl-8-nitro-1,2-dihydronaphthalene C11H10FNO2 详情 详情
(XI) 52768 3-fluoro-4-methyl-5,6,7,8-tetrahydro-1-naphthalenylamine; 3-fluoro-4-methyl-5,6,7,8-tetrahydro-1-naphthalenamine C11H14FN 详情 详情
(XII) 52769 N-(3-fluoro-4-methyl-5,6,7,8-tetrahydro-1-naphthalenyl)acetamide C13H16FNO 详情 详情
(XIII) 52770 N-(3-fluoro-4-methyl-8-oxo-5,6,7,8-tetrahydro-1-naphthalenyl)acetamide C13H14FNO2 详情 详情
(XIV) 52771 N-[3-fluoro-7-(hydroxyimino)-4-methyl-8-oxo-5,8-dihydro-1(6H)-naphthalenyl]acetamide C13H13FN2O3 详情 详情
(XV) 52772 N-[7-(acetylamino)-3-fluoro-4-methyl-8-oxo-5,6,7,8-tetrahydro-1-naphthalenyl]acetamide C15H17FN2O3 详情 详情
(XVI) 52773 2,8-diamino-6-fluoro-5-methyl-3,4-dihydro-1(2H)-naphthalenone C11H13FN2O 详情 详情
(XVII) 52774 N-(8-amino-6-fluoro-5-methyl-1-oxo-1,2,3,4-tetrahydro-2-naphthalenyl)-2,2,2-trifluoroacetamide C13H12F4N2O2 详情 详情

合成路线15

该中间体在本合成路线中的序号：

The reaction of 4-aminobenzamidine dihydrochloride (I) with succinic anhydride and pyridine in hot DMF gives the succinyl derivative (II), which is activated with isobutyl chloroformate and N-methylmorpholine (NMM) and then coupled to 3(S)-amino-4-pentynoic acid ethyl ester (III) in DMF or DMAc.

参考文献 中间体
合成目标
【1】 Zablocki, J.A.; Rico, J.G.; Garland, R.B.; et al.; Potent in vitro and in vivo inhibitors of platelet aggregation based upon the Arg-Gly-Asp sequence of fibrinogen. (Aminobenzamidino)succinyl (ABAS) series of orally active fibrinogen receptor antagonists. J Med Chem 1995, 38, 13, 2378-94.
【2】 Graul, A.; Martel, A.M.; Castaner, J.; Xemilofiban. Drugs Fut 1997, 22, 5, 508.
【3】 Bovy, P.R.; Rico, J.G.; Rogers, T.E.; Tjoeng, F.S.; Zablocki, J.A. (Pharmacia Corp.); Substd. beta-amino acid derivs. useful as platelet aggregation inhibitors. EP 0542708; EP 0614360; JP 1995500111; US 5239113; WO 9307867 .
【4】 Process for the preparation of ethyl 3S-[4[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-4-pentynoate. US 5536869 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(I) 16295 4-aminobenzenecarboximidamide hydrochloride; 4-aminobenzamidine 3858-83-1 C7H9N3 详情 详情
(II) 16296 4-[4-[amino(imino)methyl]anilino]-4-oxobutyric acid C11H13N3O3 详情 详情
(III) 16297 ethyl (3S)-3-amino-4-pentynoate C7H11NO2 详情 详情

合成路线16

该中间体在本合成路线中的序号：(XIII)

A short and efficient synthesis of xemilofiban has been achieved as follows: The reaction of ethyl chloroformate (I) with trimethylsilylacetylene (II) by means of butyllithium gives ethyl 3-(trimethylsilyl)propyonate (III), which is condensed with the lithium salt of ethyl acetate (IV) yielding ethyl 5-(trimethylsilyl)-3-oxo-4-pentynoate (V). The selective reduction of (V) with lyophilized baker's yeast (Saccharomyces cerevisiae, Sigma type II) affords ethyl 3(R)-hydroxy-5-(trimethylsilyl)-4-pentynoate (VI), which by reaction with ammonia (VII), diethyl azodicarboxylate (VIII) and triphenylphosphine, followed by hydrolysis with water gives 3(S)-amino-5-(trimethylsilyl)-4-pentynoate (IX). Finally, this compound is condensed with N-(4-amidinophenyl)succinamic acid (XI) by means of isobutyl chloroformate and N-methylmorpholine (NMM). The intermediate succinamic acid (XI) has been obtained by condensation of 4-aminobenzamidine (XII) with succinic anhydride (XIII) in DMF.

参考文献 中间体
合成目标
【1】 Cossy, J.; Schmitt, A.; Cinquin, C.; Buisson, D.; Belotti, D.; A very short, efficient and inexpensive synthesis of the prodrug form of SC-54701A a platelet aggregation inhibitor. Bioorg Med Chem Lett 1997, 7, 13, 1699.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 11229 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate 541-41-3 C3H5ClO2 详情 详情
(II) 23897 ethynyl(trimethyl)silane；trimethylsilyl acetylene 1066-54-2 C5H10Si 详情 详情
(III) 23898 ethyl 3-(trimethylsilyl)-2-propynoate 29394-58-9 C8H14O2Si 详情 详情
(IV) 23899 lithium 1-ethoxy-1-ethylenolate C4H7LiO2 详情 详情
(V) 23900 ethyl 3-oxo-5-(trimethylsilyl)-4-pentynoate C10H16O3Si 详情 详情
(VI) 23901 ethyl (3R)-3-hydroxy-5-(trimethylsilyl)-4-pentynoate C10H18O3Si 详情 详情
(VIII) 20989 Diethylazadicarboxylate; Diethyl Azodiformate; Azodiformic Acid Diethyl Ester; Diethyl Azodicarboxylate; Azodicarboxylic Acid Diethyl Ester; Diethyl 1,2-diazenedicarboxylate 1972-28-7 C6H10N2O4 详情 详情
(IX) 23904 ethyl (3S)-3-amino-5-(trimethylsilyl)-4-pentynoate C10H19NO2Si 详情 详情
(X) 16297 ethyl (3S)-3-amino-4-pentynoate C7H11NO2 详情 详情
(XI) 16296 4-[4-[amino(imino)methyl]anilino]-4-oxobutyric acid C11H13N3O3 详情 详情
(XII) 16295 4-aminobenzenecarboximidamide hydrochloride; 4-aminobenzamidine 3858-83-1 C7H9N3 详情 详情
(XIII) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线17

该中间体在本合成路线中的序号：(II)

The Friedel Craft condensation of 1,3-difluorobenzene (I) with succinic anhydride (II) gives the 4-oxobutyric acid (III); which by a Wittig reaction with methylene triphenylphosphorane (IV) yields the 4-pentenoic acid (V). The condensation of (V) with the chiral auxiliary, 4(R)-benyzloxazolidin-2-one (VI) by means of pivaloyl chloride and BuLi affords the chiral imide (VII), which is submitted to a diastereoselective hydroxymethylation with trioxane and TiCl4 in THF to provide the hydroxymethyl adduct (VIII). The direct iodocyclization of (VIII) by means of I2 and pyridine in acetonitrile gives the chiral cis-tetrahydrofuran derivative (IX). The reductive cleavage of the chiral auxiliary of (IX) by means of LiBH4 in THF yields the iodoalcohol (X)???(X)a, which is condensed with 1,2,4-triazole sodium salt (XI) to afford the adduct (XII). Finally, this compound is treated with Ts-Cl and pyridine to afford the target intermediate tosylate (XIII) (see scheme no. 20027601a, intermediate no. (II)).

参考文献 中间体
合成目标
【1】 Saksena, A.K.; Girijavallabhan, V.M.; Wang, H.Y.; Liu, Y.T.; Pike, R.E.; Ganguly, A.K.; Concise asymmetric routes to 2,2,4-trisubstituted tetrahydrofurans via chiral titanium imide enolates: Key intermediates towards synthesis of highly active azole antifungals Sch 51048 and Sch 56592. Tetrahedron Lett 1996, 37, 32, 5657.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 13095 m-Difluorobenzene; 1,3-Difluorobenzene 372-18-9 C6H4F2 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 17089 4-(2,4-difluorophenyl)-4-oxobutyric acid 110931-77-6 C10H8F2O3 详情 详情
(IV) 27301 methylene(triphenyl)phosphorane C19H17P 详情 详情
(V) 17090 4-(2,4-difluorophenyl)-4-pentenoic acid C11H10F2O2 详情 详情
(VI) 25351 (4R)-4-benzyl-1,3-oxazolidin-2-one; (R)-(+)-4-benzyl-2-oxazolidinone 102029-44-7 C10H11NO2 详情 详情
(VII) 58310 (4R)-4-benzyl-3-[4-(2,4-difluorophenyl)-4-pentenoyl]-1,3-oxazolidin-2-one C21H19F2NO3 详情 详情
(VIII) 58311 (4R)-4-benzyl-3-[(2S)-4-(2,4-difluorophenyl)-2-(hydroxymethyl)-4-pentenoyl]-1,3-oxazolidin-2-one C22H21F2NO4 详情 详情
(IX) 58312 (4R)-4-benzyl-3-{[(3S,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydro-3-furanyl]carbonyl}-1,3-oxazolidin-2-one C22H20F2INO4 详情 详情
(X) 17096 [(3R,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydro-3-furanyl]methanol C12H13F2IO2 详情 详情
(XI) 16341 1H-1,2,4-triazol-1-ylsodium C2H2N3Na 详情 详情
(XII) 16343 [(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methanol C14H15F2N3O2 详情 详情
(XIII) 16311 [(3S,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methyl 4-methylbenzenesulfonate C21H21F2N3O4S 详情 详情

合成路线18

该中间体在本合成路线中的序号：(XXXV)

3) The Friedel Crafts condensation of m-difluorobenzene (XXXIV) with succinic anhydride (XXXV) gives 4-(2,4-difluorophenyl)-4-oxobutyric acid (XXXVI), which is converted by a Wittig reaction into 4-(2,4-difluorophenyl)-4-pentenoic acid (XXXVII) and subsequently into its acyl chloride (XXXVIII). The condensation of (XXXVIII) with 4(R)-benzyloxazolidin-2-one (XXXIX) gives the acyl oxazolidinone (XL), which is regioselectively hydroxymethylated with 1,3,5-trioxane and TiCl4 to afford 4(R)-benzyl-3-[4-(2,4-difluorophenyl)-3(S)-(hydroxymethyl)-4-pentenoyl] oxazolidin-2-one (XLI). The cyclization of (XLI) with iodine and pyridine yields the tetrahydrofuran derivative (XLII), which is reduced with LiBH4 to (5R-cis)-5-(2,4-difluoromethyl)-5-(iodomethyl)tetrahydrofuran-3-methanol (XLIII). Finally, this compound is condensed with sodium 1,2,4-triazole (XXXI) to afford (5R-cis)-5-(2,4-difluoromethyl)-5-(1,2,4-triazol-1-ylmethyl) tetrahydrofuran-3-methanol (XXXIII), already obtained in Scheme 22656201c.

参考文献 中间体
合成目标
【1】 Fromtling, R.A.; Castañer, J.; SCH-56592. Drugs Fut 1996, 21, 2, 160.
【2】 Girijavallabhan, V.M.; Saksena, A.K.; Lovey, R.G.; Bennett, F.; Pike, R.E.; Wang, H.; Pinto, P.; Liu, Y.T.; Patel, N.; Ganguly, A.K.; SCH-56592, a novel orally active broad spectrum antifungal agent. 35th Intersci Conf Antimicrob Agents Chemother (Sept 17-20, San Francisco) 1995, Abst F61.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IXL) 17092 (4R)-4-heptyl-1,3-oxazolan-2-one C10H19NO2 详情 详情
(XXXI) 13104 1,2,4-Triazole, sodium derivative 41253-21-8 C2H2N3Na 详情 详情
(XXXIII) 16343 [(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methanol C14H15F2N3O2 详情 详情
(XXXIV) 13095 m-Difluorobenzene; 1,3-Difluorobenzene 372-18-9 C6H4F2 详情 详情
(XXXV) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(XXXVI) 17089 4-(2,4-difluorophenyl)-4-oxobutyric acid 110931-77-6 C10H8F2O3 详情 详情
(XXXVII) 17090 4-(2,4-difluorophenyl)-4-pentenoic acid C11H10F2O2 详情 详情
(XXXVIII) 17091 4-(2,4-difluorophenyl)-4-pentenoyl chloride C11H9ClF2O 详情 详情
(XXXIX) 17092 (4R)-4-heptyl-1,3-oxazolan-2-one C10H19NO2 详情 详情
(XL) 17093 (4R)-3-[4-(2,4-difluorophenyl)-4-pentenoyl]-4-heptyl-1,3-oxazolan-2-one C21H27F2NO3 详情 详情
(XLI) 17094 (4R)-3-[(2S)-4-(2,4-difluorophenyl)-2-(hydroxymethyl)-4-pentenoyl]-4-heptyl-1,3-oxazolan-2-one C22H29F2NO4 详情 详情
(XLII) 17095 (4R)-3-[[(3S,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydro-3-furanyl]carbonyl]-4-heptyl-1,3-oxazolan-2-one C22H28F2INO4 详情 详情
(XLIII) 17096 [(3R,5R)-5-(2,4-difluorophenyl)-5-(iodomethyl)tetrahydro-3-furanyl]methanol C12H13F2IO2 详情 详情

合成路线19

该中间体在本合成路线中的序号：(II)

The Friedel Craft's condensation of 2-methyl-2-phenylpropionic acid methyl ester (I) with succinic anhydride (II) by means of AlCl3 in CS2 or dichloromethane/nitrobenzene gives 2-[4-(hydroxysuccinyl)phenyl]-2-methylpropionic acid methyl ester (III) (purified through its phenethylamine salt), which is condensed with 4-(1-hydroxy-1,1-diphenylmethyl)piperidine (IV) by means of ethyl chloroformate and TEA in THF or with DCC and p-nitrophenol in ethyl acetate to yield the adduct (V). The reduction of the oxo groups of (V) by means of BH3/Me2S in THF affords the ester precursor (VI), which is finally hydrolyzed with NaOH in refluxing methanol to provide the target compound.

参考文献 中间体
合成目标
【1】 Schroeder, C.; Huddleston, R.; Charles, R. (Aventis Pharma Deutschland GmbH); Process for the production of the piperidine deriv. fexofenadine. WO 02102776 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 58227 methyl 2-methyl-2-phenylpropanoate; Methyl alpha,alpha-dimethylbenzeneacetate C11H14O2 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(III) 58228 4-[4-(2-methoxy-1,1-dimethyl-2-oxoethyl)phenyl]-4-oxobutanoic acid C15H18O5 详情 详情
(IV) 17178 diphenyl(4-piperidinyl)methanol; alpha,alpha-Diphenyl-4-piperidinomethanol; Azacyclonol 115-46-8 C18H21NO 详情 详情
(V) 58229 methyl 2-[4-(4-{4-[hydroxy(diphenyl)methyl]-1-piperidinyl}-4-oxobutanoyl)phenyl]-2-methylpropanoate C33H37NO5 详情 详情
(VI) 58230 methyl 2-[4-(1-hydroxy-4-{4-[hydroxy(diphenyl)methyl]-1-piperidinyl}butyl)phenyl]-2-methylpropanoate C33H41NO4 详情 详情

合成路线20

该中间体在本合成路线中的序号：(V)

The condensation of doxorubicin (I) with Fmoc-beta-alanyl-L-leucyl-L-alanyl-L-leucine (II) by means of HATU and DIEA in DMF gives the protected adduct (III), which is treated with piperidine in DMF to yield the deprotected adduct (IV). Finally, this compound is condensed with succinic anhydride (V) in the same solvent and treated with NaOH or NaHCO3 to afford the target sodium salt.

参考文献 中间体
合成目标
【1】 Fernandez, A.-M.; et al.; N-Succinyl-(beta-alanyl-L-leucyl-L-alanyl-L-leucyl)doxorubicin: An extracellularly tumor-activated prodrug devoid of intravenous acute toxicity. J Med Chem 2001, 44, 22, 3750.
【2】 Lobl, T.J.; Trouet, A.; Fernandez, A.-M.; Nieder, M.H.; Yarranton, G.T.; Gangwar, S.; Viski, P.; Lewis, E.; Dubois, V. (Beckman Coulter, Inc.); Prodrug cpds. and process for preparation thereof. WO 0033888 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 49366 (9S,12S,15S)-1-(9H-fluoren-9-yl)-9,15-diisobutyl-12-methyl-3,7,10,13-tetraoxo-2-oxa-4,8,11,14-tetraazahexadecan-16-oic acid C33H44N4O7 详情 详情
(II) 11675 (8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione C27H29NO11 详情 详情
(III) 49367 9H-fluoren-9-ylmethyl 3-([(1S)-1-[([(1S)-2-[((1S)-1-[[((2S,3S,4S,6R)-6-[[(1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)amino]carbonyl]-3-methylbutyl)amino]-1-methyl-2-oxoethyl]amino)carbonyl]-3-methylbutyl]amino)-3-oxopropylcarbamate C60H71N5O17 详情 详情
(IV) 49368 (2S)-2-[(3-aminopropanoyl)amino]-N-[(1S)-2-[((1S)-1-[[((2S,3S,4S,6R)-6-[[(1S,3S)-3-glycoloyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-naphthacenyl]oxy]-3-hydroxy-2-methyltetrahydro-2H-pyran-4-yl)amino]carbonyl]-3-methylbutyl)amino]-1-methyl-2-oxoethyl]-4-methylpentanamide C45H61N5O15 详情 详情
(V) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线21

该中间体在本合成路线中的序号：(II)

Esterification of probucol (I) with succinic anhydride (II) in the presence of NaH afforded the title monosuccinate ester, which was separated from the unreacted probucol (I) and the corresponding disuccinate ester by column chromatography. Esterification of (I) was also reported in the presence of other bases, such as potassium tert-butoxide, KOH, DMAP and DABCO.

参考文献 中间体
合成目标
【2】 Meng, C.Q.; Somers, P.K.; Rachita, C.L.; Holt, L.A.; Hoong, L.K.; Zehng, X.S.; Simpson, J.E.; Hill, R.R.; Olliff, L.K.; Kunsch, C.; Sundell, C.L.; Parthasarathy, S.; Saxena, U.; Sikorski, J.A.; Wasserman, M.A.; Novel phenolic antioxidants as multifunctional inhibitors of inducible VCAM-1 expression for use in atherosclerosis. Bioorg Med Chem Lett 2002, 12, 18, 2545.
【1】 Sorbera, L.A.; Castaner, J.; AGI-1067. Drugs Fut 2003, 28, 5, 421.
【3】 Jass, P.A.; Process for preparing probucol derivs.. US 6323359 .
【4】 Medford, R.M.; Meng, C.Q.; Hoong, L.K.; Somers, P.K. (AtheroGenics, Inc.); Cpds. and methods for the inhibition of the expression of VCAM-1. JP 2002503227; US 6147250; WO 9851662 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 55055 2,6-di(tert-butyl)-4-[(1-{[3,5-di(tert-butyl)-4-hydroxyphenyl]sulfanyl}-1-methylethyl)sulfanyl]phenol C31H48O2S2 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线22

该中间体在本合成路线中的序号：(I)

The reaction of succinic anhydride (I) with the lithium salt of the chiral oxazolidinone (II) in THF gives 3-(hydroxysucccinyl)-4(S)-isopropyloxazolidin-2-one (III), which is treated successively with oxalyl chloride, CH2N2 and HBr to yield the bromomethyl derivative (IV). The cyclization of (IV) with thiourea in refluxing isopropanol affords the 2-aminothiazol derivative (V), which is protected with 2,2,2-trichloroethyl chloroformate by means of DIEA and DMAP in dichloromethane giving the carbamate (VI). The reaction of (VI) with tert-butyl 2-bromoacetate (VII) by means of sodium hexamethyldisilazane (NaHMDS) in THF yields the chiral butyrate (VIII), which is hydrolyzed with TFA in dichloromethane to the chiral butyric acid (IX). The condensation of (IX) with the intermediate amine (X) by means of BOP-PF6 and DIEA in DMF affords the corresponding amide (XI), which is treated with magnesium methoxide in methanol to eliminate the oxazolidinone group (the chiral inductor) providing the methyl ester (XII). The hydrolysis of (XII) with NaOH, followed by condensation with amine (XIII) (J Org Chem 1988, 53: 6109; J Med Chem 1993, 36: 449) gives the protected intermediate (XIV), which is finally deprotected by reaction with Zn/HCl in aqueous dioxane.

参考文献 中间体
合成目标
【1】 Simoneau, B.; Lavallee, P.; Anderson, P.C.; et al.; Discovery of non-peptidic P2-P3 butanediamide renin inhibitors with high oral efficacy. Bioorg Med Chem 1999, 7, 3, 489.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
10180 Thiourea 62-56-6 CH4N2S 详情 详情
13664 1,1,1-Trichloro-2-[(chlorocarbonyl)oxy]ethane; 2,2,2-Trichloroethyl chloroformate 17341-93-4 C3H2Cl4O2 详情 详情
(I) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(II) 29533 [(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]lithium C6H10LiNO2 详情 详情
(III) 29534 4-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutyric acid C10H15NO5 详情 详情
(IV) 29535 5-bromo-1-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-1,4-pentanedione C11H16BrNO4 详情 详情
(V) 29536 (4S)-3-[3-(2-amino-1,3-thiazol-4-yl)propanoyl]-4-isopropyl-1,3-oxazolidin-2-one C12H17N3O3S 详情 详情
(VI) 29537 2,2,2-trichloroethyl 4-[3-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-3-oxopropyl]-1,3-thiazol-2-ylcarbamate C15H18Cl3N3O5S 详情 详情
(VII) 17430 2-Bromoacetic acid tert-butyl ester; tert-butyl 2-bromoacetate; tert-Butyl bromoacetate 5292-43-3 C6H11BrO2 详情 详情
(VIII) 29538 tert-butyl (3R)-4-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxo-3-[(2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1,3-thiazol-4-yl)methyl]butanoate C21H28Cl3N3O7S 详情 详情
(IX) 29539 (3R)-4-[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxo-3-[(2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1,3-thiazol-4-yl)methyl]butyric acid C17H20Cl3N3O7S 详情 详情
(X) 29540 2-[(cyclohexylmethyl)amino]-N-methyl-N-[2-(2-pyridinyl)ethyl]acetamide C17H27N3O 详情 详情
(XI) 29541 2,2,2-trichloroethyl 4-((2R)-4-[(cyclohexylmethyl)(2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl)amino]-2-[[(4S)-4-isopropyl-2-oxo-1,3-oxazolidin-3-yl]carbonyl]-4-oxobutyl)-1,3-thiazol-2-ylcarbamate C34H45Cl3N6O7S 详情 详情
(XII) 29542 methyl (2R)-4-[(cyclohexylmethyl)(2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl)amino]-4-oxo-2-[(2-[[(2,2,2-trichloroethoxy)carbonyl]amino]-1,3-thiazol-4-yl)methyl]butanoate C29H38Cl3N5O6S 详情 详情
(XIII) 29543 (2S,3R,4S)-2-amino-1-cyclohexyl-6-methyl-3,4-heptanediol C14H29NO2 详情 详情
(XIV) 29544 2,2,2-trichloroethyl 4-[(2R)-2-([[(1S,2R,3S)-1-(cyclohexylmethyl)-2,3-dihydroxy-5-methylhexyl]amino]carbonyl)-4-[(cyclohexylmethyl)(2-[methyl[2-(2-pyridinyl)ethyl]amino]-2-oxoethyl)amino]-4-oxobutyl]-1,3-thiazol-2-ylcarbamate C42H63Cl3N6O7S 详情 详情

合成路线23

该中间体在本合成路线中的序号：(II)

By condensation of biphenyl (I) and succinic anhydride (II) in nitrobenzene, using AlCl3, as catalyst.

参考文献 中间体
合成目标
【1】 Castañer, J.; Fenbufen. Drugs Fut 1976, 1, 1, 21.
【2】 Tomeufeik, A.; et al. (American Cyanamid Co.); Compositions containing substituted benzoylpropionic acids and method of use to treat inflammation and pain. DE 2147111; FR 2107848; GB 1320076; US 3784701 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
22523 1-nitrobenzene 28250-14-8 C6H5NO2 详情 详情
(I) 31202 1,1'-biphenyl 92-52-4 C12H10 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线24

该中间体在本合成路线中的序号：(II)

The title compound is a semisynthetic derivative of triptolide (I), a substance isolated from the root xylem of the Chinese medicinal plant Tripterygium wilfordii. Condensation of (I) with succinic anhydride (II) in hot pyridine furnished the corresponding hemisuccinate ester. This was converted to the corresponding sodium salt by treatment with aqueous NaHCO3 and then isolated by lyophilization of the filtered solution.

参考文献 中间体
合成目标
【1】 Qi, Y.M.; Musser, J.H.; Fidler, J.M. (Pharmagenesis, Inc.); Immunosuppressive cpds. and methods. EP 0907652; JP 2001504437; US 5663335; US 5962516; WO 9731920; WO 9731921 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 51397 (3bS,4aS,5aS,6S,6aR,7aS,7bS,8aS,8bS)-6-hydroxy-6a-isopropyl-8b-methyl-3b,4,4a,6,6a,7a,7b,8b,9,10-decahydrotrioxireno[2',3':6,7:2',3':8a,9:2',3':4b,5]phenanthro[1,2-c]furan-1(3H)-one C20H24O6 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线25

该中间体在本合成路线中的序号：(VI)

Coupling of PhCH2OOC-Pro-OH (I) with diphenyl (1-amino-2-phenylethyl)phosphonate (II) by means of DCC in THF affords derivative (III), which is then subjected to hydrogenation followed by coupling with PhCH2OOC -Val-OH (IV) by means of DCC to provide peptide derivative (V). Finally, reaction of (V) with succinic anhydride in EtOAc under an atmosphere of H2 in the presence of Pd/C provides the target compound.

参考文献 中间体
合成目标
【1】 Oleksyszym, J.; Powers, J.C.; Irreversible inhibition of serine proteases by peptide derivatives of (alpha-aminoalkyl)phosphonate diphenyl esters. Biochemistry 1991, 30, 2, 485.
【2】 Powers, J.C.; Ni, L.; Jackson, D.S. (Georgia Technology Research Corp.); Basic alpha-aminoalkylphosphonate derivs.. US 5952307 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 19113 (2S)-1-[(benzyloxy)carbonyl]-2-pyrrolidinecarboxylic acid 1148-11-4 C13H15NO4 详情 详情
(II) 44216 diphenyl (1R)-1-amino-2-phenylethylphosphonate C20H20NO3P 详情 详情
(III) 44217 benzyl (2S)-2-([[(1R)-1-(diphenoxyphosphoryl)-2-phenylethyl]amino]carbonyl)-1-pyrrolidinecarboxylate C33H33N2O6P 详情 详情
(IV) 18092 (2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutyric acid C13H17NO4 详情 详情
(V) 44218 diphenyl (1R)-1-([[(2S)-1-((2S)-2-[[(benzyloxy)carbonyl]amino]-3-methylbutanoyl)pyrrolidinyl]carbonyl]amino)-2-phenylethylphosphonate C38H42N3O7P 详情 详情
(VI) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线26

该中间体在本合成路线中的序号：(III)

5-Iodo-2'-deoxyuridine (I) is protected at the primary hydroxyl group with 4,4'-dimethoxytrityl chloride to afford the 5'-O-trityl derivative (II). Subsequent esterification of the remaining hydroxyl group of (II) with succinic anhydride (III) yields the succinate mono-ester (IV). Acid (IV) is then coupled with diethylene glycol in the presence of DCC to produce (V). The O-trityl group of (V) is finally removed by treatment with formic acid, to give the title compound.

参考文献 中间体
合成目标
【1】 Bonina, F.P.; et al.; New oligoethylene ester derivatives of 5-iodo-2'-deoxyuridine as dermal prodrugs: Synthesis, physicochemical properties, and skin permeation studies. J Pharm Sci 2002, 91, 1, 171.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 31154 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione 54-42-2 C9H11IN2O5 详情 详情
(II) 57566 1-((2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydro-2-furanyl)-5-iodo-2,4(1H,3H)-pyrimidinedione C30H29IN2O7 详情 详情
(III) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(IV) 57567 4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid C34H33IN2O10 详情 详情
(V) 57568 1-{(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl} 4-[2-(2-hydroxyethoxy)ethyl] succinate C38H41IN2O12 详情 详情

合成路线27

该中间体在本合成路线中的序号：(III)

5-Iodo-2'-deoxyuridine (I) is protected at the primary hydroxyl group with 4,4'-dimethoxytrityl chloride to afford the 5'-O-trityl derivative (II). Subsequent esterification of the remaining hydroxyl group of (II) with succinic anhydride (III) yields the succinate mono-ester (IV). Acid (IV) is then coupled with triethylene glycol in the presence of DCC to produce (V). The O-trityl group of (V) is finally removed by treatment with formic acid, to give the title compound.

参考文献 中间体
合成目标
【1】 Bonina, F.P.; et al.; New oligoethylene ester derivatives of 5-iodo-2'-deoxyuridine as dermal prodrugs: Synthesis, physicochemical properties, and skin permeation studies. J Pharm Sci 2002, 91, 1, 171.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 31154 1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydro-2-furanyl]-5-iodo-2,4(1H,3H)-pyrimidinedione 54-42-2 C9H11IN2O5 详情 详情
(II) 57566 1-((2R,4S,5R)-5-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-4-hydroxytetrahydro-2-furanyl)-5-iodo-2,4(1H,3H)-pyrimidinedione C30H29IN2O7 详情 详情
(III) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(IV) 57567 4-({(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl}oxy)-4-oxobutanoic acid C34H33IN2O10 详情 详情
(V) 57569 1-{(2R,3S,5R)-2-{[bis(4-methoxyphenyl)(phenyl)methoxy]methyl}-5-[5-iodo-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]tetrahydro-3-furanyl} 4-{2-[2-(2-hydroxyethoxy)ethoxy]ethyl} succinate C40H45IN2O13 详情 详情

合成路线28

该中间体在本合成路线中的序号：(VI)

Condensation of paclitaxel (V) with succinic anhydride (VI) affords the hemisuccinate ester (VII). This is subsequently coupled with amino ester (IV) in the presence of DCC to furnish the title compound.

参考文献 中间体
合成目标
【1】 Jacob, J.N. (Organomed Corporation); Paclitaxel-carbohydrate conjugates: Design, synthesis and biological evaluations. US 6218367 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IV) 59013 (3R,4S,5R,6R)-2,3,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl 4-aminobutanoate C10H19NO7 详情 详情
(V) 10595 (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetoxy)-15-[[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0(3,10).0(4,7)]heptadec-13-en-2-yl benzoate 33069-62-4 C47H51NO14 详情 详情
(VI) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
(VII) 59014 4-{[(1R,2S)-2-(benzoylamino)-1-({[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-2-(benzoyloxy)-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0~3,10~.0~4,7~]heptadec-13-en-15-yl]oxy}carbonyl)-2-phenylethyl]oxy}-4-oxobutano C51H55NO17 详情 详情

合成路线29

该中间体在本合成路线中的序号：(II)

Tetrahydrocannabinol hemisuccinate is prepared by acylation of tetrahydrocannabinol (I) with succinic anhydride (II) in the presence of a variety of organic and inorganic bases.

参考文献 中间体
合成目标
【1】 Elsohly, M.A.; Ross, S.A.; Feng, S. (University of Mississippi); Method of preparing delta-9-tetrahydrocannabinol esters. GB 2358397; US 6008383; WO 0029402 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 58450 (6aR,10aR)-6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydro-6H-benzo[c]chromen-1-ol; delta 1-tetrahydrocannabinol C21H30O2 详情 详情
(II) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情

合成路线30

该中间体在本合成路线中的序号：(VIII)

Hydroboration of the double bond of (VI), followed by quenching with NaBO3 yields the primary alcohol (VII). This is then acylated by succinic anhydride (VIII) in the presence of DMAP to provide the target succinate ester.

参考文献 中间体
合成目标
【1】 Posner, G.H.; Paik, I.-P.; Sur, S.; McRiner, A.J.; Borstnik, K.; Zie, S.; Shapiro, T.A.; Orally active, antimalarial, anticancer, artemisinin-derived trioxane dimers with high stability and efficacy. J Med Chem 2003, 46, 6, 1060.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VI) 64028 (1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-10-(2-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]methyl}-2-propenyl)-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadecane C34H52O8 详情 详情
(VII) 64030 3-[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]-2-{[(1R,4S,5R,8S,9R,10R,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.0~4,13~.0~8,13~]hexadec-10-yl]methyl}-1-propanol C34H54O9 详情 详情
(VIII) 11291 Dihydro-2,5-furandione; Succinic anhydride 108-30-5 C4H4O3 详情 详情
Extended Information