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【结 构 式】 
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【分子编号】35333 【品名】ethyl propiolate 【CA登记号】623-47-2 |
【 分 子 式 】C5H6O2 【 分 子 量 】98.10144 【元素组成】C 61.22% H 6.16% O 32.62% |
合成路线1
该中间体在本合成路线中的序号：(V)The condensation of verbenone (I) with 1-bromo-3-methyl-2-butene (II) by means of t-BuOK in DME, followed by ozonolysis of the aliphatic double bond gives acetaldehyde (III), which is isomerized with UV light in methanol to the chrysanthenone derivative (IV). The condensation of (IV) with ethyl propynoate (V) by means of LDA in THF, followed by silylation with TMSCl affords the silylated 4-hydroxy-2-pentynoate (VI), which is cyclized by means of Me2CuLi in ethyl ether giving the methanonaphthalene derivative (VII). The oxidation of the secondary OH group of (VII) with Dess Martin periodinane (DMP) yields the ketoester (VIII), which is hydroxylated with Davis' oxaziridine to the ketonic dihydroxyester (IX). The reduction of the ester group of (IX) with LiAlH4 in ethyl ether affords the tetrahydroxy compound (X), which is protected by silylation with TBDMS-Cl and imidazole and ketalization with PPTS and 2-methoxypropene providing the silylated acetonide (XI). The rearrangement of (XI) by means of MCPBA, followed by silylation with Tips-OTf gives (XII) with the A-B-bicycle of Taxol. The hydroxylation of (XII) with t-BuOK and oxygen, followed by reduction of its ketonic group with NaBH4 yields the trihydroxy compound (XIII), which is stereoselectively reduced with H2 and Crabtree catalyst, silylated with TMSCl and treated with triphosgene to afford the cyclic carbonate (XIV). The oxidation of (XIV) with pyridinium chlorochromate (PCC) in dichloromethane gives the carbaldehyde (XV), which is condensed with methoxymethyl(triphenyl)phosphorane to yield the acetaldehyde derivative (XVI). The selective silylation of (XVI) with Tes-Cl, followed by oxidation of the remaining secondary OH group with Dess Martin periodinane (DMP) and methylenation acetaldehyde CH2 group with Me2N-CH2-I affords the substituted propenoic aldehyde (XVII).
| 【1】 Wender, P.A.; et al.; The pinene path to taxanes. 5. Stereocontrolled synthesis of a versatile taxane precursor. J Am Chem Soc 1997, 119, 11, 2755. |
| 【2】 Wender, P.A.; et al.; The pinene path to taxanes. 6. Concise stereocontrolled synthesis of Taxol. J Am Chem Soc 1997, 119, 11, 2757. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 17354 | isopropenyl methyl ether; 2-methoxy-1-propene | 116-11-0 | C4H8O | 详情 | 详情 | |
| 40589 | methyl (triphenylphosphoranylidene)methyl ether; (methoxymethylene)(triphenyl)phosphorane | C20H19OP | 详情 | 详情 | ||
| 40590 | iodo-N,N-dimethylmethanamine; N-(iodomethyl)-N,N-dimethylamine | C3H8IN | 详情 | 详情 | ||
| (I) | 35330 | 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one | 1196-01-6 | C10H14O | 详情 | 详情 |
| (II) | 12989 | 4-Bromo-2-methyl-2-butene; 1-Bromo-3-methyl-2-butene | 870-63-3 | C5H9Br | 详情 | 详情 |
| (III) | 35331 | 2-(2,6,6-trimethyl-4-oxobicyclo[3.1.1]hept-2-en-3-yl)acetaldehyde | C12H16O2 | 详情 | 详情 | |
| (IV) | 35332 | 2-(2,6,6-trimethyl-7-oxobicyclo[3.1.1]hept-2-en-1-yl)acetaldehyde | C12H16O2 | 详情 | 详情 | |
| (V) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (VI) | 35334 | ethyl 5-(2,6,6-trimethyl-7-oxobicyclo[3.1.1]hept-2-en-1-yl)-4-[(trimethylsilyl)oxy]-2-pentynoate | C20H30O4Si | 详情 | 详情 | |
| (VII) | 35335 | ethyl (6R)-3,6-dihydroxy-4,10,11,11-tetramethyltricyclo[5.3.1.0(1,6)]undeca-4,9-diene-5-carboxylate | C18H26O4 | 详情 | 详情 | |
| (VIII) | 35336 | ethyl (6R)-6-hydroxy-4,10,11,11-tetramethyl-3-oxotricyclo[5.3.1.0(1,6)]undeca-4,9-diene-5-carboxylate | C18H24O4 | 详情 | 详情 | |
| (IX) | 35337 | ethyl (2S,6R)-2,6-dihydroxy-4,10,11,11-tetramethyl-3-oxotricyclo[5.3.1.0(1,6)]undeca-4,9-diene-5-carboxylate | C18H24O5 | 详情 | 详情 | |
| (X) | 35338 | (2S,3S,6S)-5-(hydroxymethyl)-4,10,11,11-tetramethyltricyclo[5.3.1.0(1,6)]undeca-4,9-diene-2,3,6-triol | C16H24O4 | 详情 | 详情 | |
| (XI) | 35339 | (2S,6S,9S)-8-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4,4,7,13,14,14-hexamethyl-3,5-dioxatetracyclo[8.3.1.0(1,9).0(2,6)]tetradeca-7,12-dien-9-ol | C25H42O4Si | 详情 | 详情 | |
| (XII) | 35340 | (2S,6S,12S)-8-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4,4,7,13,14,14-hexamethyl-12-[(triisopropylsilyl)oxy]-3,5-dioxatricyclo[8.3.1.0(2,6)]tetradeca-1(13),7-dien-9-one | C34H62O5Si2 | 详情 | 详情 | |
| (XIII) | 35341 | (2S,6S,9S,10S,12S)-8-(hydroxymethyl)-4,4,7,13,14,14-hexamethyl-12-[(triisopropylsilyl)oxy]-3,5-dioxatricyclo[8.3.1.0(2,6)]tetradeca-1(13),7-diene-9,10-diol | C28H50O6Si | 详情 | 详情 | |
| (XIV) | 35342 | (1S,5S,6S,7S,8S,12S,15S)-7,10,10,14,17,17-hexamethyl-15-[(triisopropylsilyl)oxy]-6-[[(trimethylsilyl)oxy]methyl]-2,4,9,11-tetraoxatetracyclo[11.3.1.0(1,5).0(8,12)]heptadec-13-en-3-one | C32H58O7Si2 | 详情 | 详情 | |
| (XV) | 35343 | (1S,5S,6R,7S,8S,12S,15S)-7,10,10,14,17,17-hexamethyl-3-oxo-15-[(triisopropylsilyl)oxy]-2,4,9,11-tetraoxatetracyclo[11.3.1.0(1,5).0(8,12)]heptadec-13-ene-6-carbaldehyde | C29H48O7Si | 详情 | 详情 | |
| (XVI) | 35344 | 2-[(1S,5S,6R,7S,8S,9S,12S)-8,9-dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-[(triisopropylsilyl)oxy]-2,4-dioxatricyclo[8.3.1.0(1,5)]tetradec-10-en-6-yl]acetaldehyde | C27H46O7Si | 详情 | 详情 | |
| (XVII) | 35345 | 2-[(1S,5S,6S,7S,8S,12S)-7,11,14,14-tetramethyl-3,9-dioxo-8-[(triethylsilyl)oxy]-12-[(triisopropylsilyl)oxy]-2,4-dioxatricyclo[8.3.1.0(1,5)]tetradec-10-en-6-yl]acrylaldehyde | C34H58O7Si2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XX)Synthesis of ketone (XXIV): Reaction of the known diol (XV) obtained by degradation of vitamin D2 with TsOH in pyridine gives, regioselectively, the monotosylate (XVI), which is protected at the secondary OH group by silylation with TBDMS-Cl and imidazole to yield the silyl ether (XVII). Oxidation of the tosyloxy group of (XVII) with O2 and t-BuOK in DMSO/t-BuOH affords ketone (XVIII), which is reduced with K and i-PrOH providing alcohol (XIX). Condensation of compound (XIX) with ethyl prop-ynoate (XX) by means of NMM in benzene gives the alkoxyacrylate (XXI), which is reduced with H2 over Pd/C in EtOH to yield the alkoxypropionate (XXII). Deprotection of the OH group of (XXII) with HF in acetonitrile affords alcohol (XXIII), which is oxidized with pyridinium dichromate (PDC) in CH2Cl2 providing ketone (XXIV). Wittig-Horner condensation of ketone (XXIV) with phosphine oxide (XIV) by means of BuLi in THF yields the corresponding adduct (XXV), which is submitted to a Grignard reaction with MeLi in THF to give the protected maxacalcitol precursor (XXVI). Finally, this compound is desilylated by means of TBAF in THF.
| 【1】 Vidal, B.; Fall, Y.; Mourino, A.; Gonzalez, V.; Stereoselective synthesis of 22-oxacalcitriol (OCT) and analogues modified at C25. Tetrahedron Lett 2002, 43, 3, 427. |
| 【2】 Fall, Y.; A new approach to the synthesis of the 25-hydroxy-22-oxa-vitamin D3 side chain. Tetrahedron Lett 1997, 38, 27, 4909. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIV) | 42574 | [2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethyl](oxo)diphenylphosphorane; 2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethyl(diphenyl)phosphine oxide | C33H51O3PSi2 | 详情 | 详情 | |
| (XV) | 52151 | (1R,3aR,4S,7aR)-1-[(1S)-2-hydroxy-1-methylethyl]-7a-methyloctahydro-1H-inden-4-ol | C13H24O2 | 详情 | 详情 | |
| (XVI) | 52152 | (2S)-2-[(1R,3aR,4S,7aR)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl]propyl 4-methylbenzenesulfonate | C20H30O4S | 详情 | 详情 | |
| (XVII) | 52153 | (2S)-2-((1R,3aR,4S,7aR)-4-[[tert-butyl(dimethyl)silyl]oxy]-7a-methyloctahydro-1H-inden-1-yl)propyl 4-methylbenzenesulfonate | C26H44O4SSi | 详情 | 详情 | |
| (XVIII) | 52154 | 1-((1S,3aR,4S,7aS)-4-[[tert-butyl(dimethyl)silyl]oxy]-7a-methyloctahydro-1H-inden-1-yl)-1-ethanone | C18H34O2Si | 详情 | 详情 | |
| (XIX) | 52155 | (1S)-1-((1S,3aR,4S,7aR)-4-[[tert-butyl(dimethyl)silyl]oxy]-7a-methyloctahydro-1H-inden-1-yl)-1-ethanol | C18H36O2Si | 详情 | 详情 | |
| (XX) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (XXI) | 52156 | ethyl (E)-3-[[(1S)-1-((1S,3aR,4S,7aR)-4-[[tert-butyl(dimethyl)silyl]oxy]-7a-methyloctahydro-1H-inden-1-yl)ethyl]oxy]-2-propenoate | C23H42O4Si | 详情 | 详情 | |
| (XXII) | 52157 | ethyl 3-[[(1S)-1-((1S,3aR,4S,7aR)-4-[[tert-butyl(dimethyl)silyl]oxy]-7a-methyloctahydro-1H-inden-1-yl)ethyl]oxy]propanoate | C23H44O4Si | 详情 | 详情 | |
| (XXIII) | 52158 | ethyl 3-([(1S)-1-[(1S,3aR,4S,7aS)-4-hydroxy-7a-methyloctahydro-1H-inden-1-yl]ethyl]oxy)propanoate | C17H30O4 | 详情 | 详情 | |
| (XXIV) | 52159 | ethyl 3-([(1S)-1-[(1S,3aR,7aR)-7a-methyl-4-oxooctahydro-1H-inden-1-yl]ethyl]oxy)propanoate | C17H28O4 | 详情 | 详情 | |
| (XXV) | 52160 | ethyl 3-[((1S)-1-[(1S,3aS,7aS)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]ethyl)oxy]propanoate | C38H68O5Si2 | 详情 | 详情 | |
| (XXVI) | 11724 | 4-[((1S)-1-[(1S,3aS,7aS)-4-[(E)-2-((3S,5R)-3,5-Bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]ethyl)oxy]-2-methyl-2-butanol | C38H70O4Si2 | 详情 | 详情 |
合成路线3
该中间体在本合成路线中的序号：(II)Cyclocondensation of a mixture of benzylamine (I), ethyl propiolate (II) and benzaldehyde (III) in hot AcOH furnished dihydropyridine (IV). Photodimerization of this compound in a MeOH-THF solution gave rise to the cage dimer (V). Finally, reduction of the ester groups of (V) by means of LiAlH4 at low temperature produced the title tetraol compound.
| 【1】 Wiese, M.; Billich, A.; Hilgeroth, A.; Synthesis and biological evaluation of the first N-alkyl cage dimeric 4-aryl-1,4-dihydropyridines as novel nonpeptidic HIV-1 protease inhibitors. J Med Chem 1999, 42, 22, 4729. |
| 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) | 15147 | Benzylamine; Phenylmethanamine | 100-46-9 | C7H9N | 详情 | 详情 |
| (II) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (III) | 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 |
| (IV) | 40525 | diethyl 1-benzyl-4-phenyl-1,4-dihydro-3,5-pyridinedicarboxylate | C24H25NO4 | 详情 | 详情 | |
| (V) | 40526 | C48H50N2O8 | 详情 | 详情 |
合成路线4
该中间体在本合成路线中的序号：(I)Isoxazolin-5-one (III) was synthesized from ethyl propiolate (I) via ethyl malonaldehyde oxime (II) by a known method. Treatment of N-Boc-L-serine (IV) with N,N-dimethylformamide di-tert-butylacetal (V) in refluxing benzene produced Boc-serine tert-butyl ester (VI) along with a small amount of O-formyl derivative, which was separated by column chromatography. Mitsunobu coupling of isoxazolinone (III) with serine derivative (VI) employing diisopropyl azodicarboxylate (DIAD) and triphenylphosphine afforded the protected O-isoxazolyl serine (VII). The protecting groups of (VII) were finally removed by treatment with trifluoroacetic acid.
| 【1】 Ikegami, F.; et al.; Synthesis and pharmacological activity of O-(5-isoxazolyl)-L-serine. Chem Pharm Bull 2000, 48, 2, 278. |
| 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) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (II) | 40205 | ethyl 3-(hydroxyimino)propanoate | C5H9NO3 | 详情 | 详情 | |
| (III) | 40206 | 5(4H)-isoxazolone | C3H3NO2 | 详情 | 详情 | |
| (IV) | 20126 | (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropionic acid | C8H15NO5 | 详情 | 详情 | |
| (V) | 21059 | N-[di(tert-butoxy)methyl]-N,N-dimethylamine; di(tert-butoxy)-N,N-dimethylmethanamine | 36805-97-7 | C11H25NO2 | 详情 | 详情 |
| (VI) | 40207 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-hydroxypropanoate | C12H23NO5 | 详情 | 详情 | |
| (VII) | 40208 | tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(5-isoxazolyloxy)propanoate | C15H24N2O6 | 详情 | 详情 |
合成路线5
该中间体在本合成路线中的序号：(IV)Boc-Leucine (I) was converted to Weinreb amide (II) by activation with isobutyl chloroformate and N-methylpiperidine, followed by treatment of the resulting mixed anhydride with N,O-dimethylhydroxylamine. Reduction of (II) with LiAlH4 provided the aldehyde (III), which was condensed with the lithium anion of ethyl propiolate (IV) to furnish the acetylenic alcohol (Va-b) as an inseparable mixture of diastereomers. Catalytic hydrogenation of the triple bond of (Va-b) over Pd/BaSO4, followed by acid-catalyzed lactonization of the resulting hydroxy ester provided the diastereomeric mixture of gamma-lactones (VIa-b). After separation by column chromatography, alkylation of the desired isomer employing iodomethane and lithium hexamethyldisilazide at -78 C provided the desired alpha-methyl lactone (VII), along with a small amount of the corresponding epimer. Lactone (VII) hydrolysis using LiOH gave hydroxy acid (VIII), which was further protected as the silyl ether (IX) with tert-butyldimethylsilyl chloride and imidazole. The Boc protecting group of (IX) was selectively removed by treatment with trifluoroacetic acid in CH2Cl2 at 0 C, and the resulting amine (X) was treated with Fmoc-succinimide to provide the Fmoc-protected intermediate (XI).
| 【1】 Lin, X.; Shin, D.; Downs, D.; Tang, J.; Koelsch, G.; Ghosh, A.K.; Ermolieff, J.; Design of potent inhibitors for human brain memapsin 2 (beta-secretase). J Am Chem Soc 2000, 122, 14, 3522. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (Va) | 40625 | ethyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyl-2-octynoate | C16H27NO5 | 详情 | 详情 | |
| (Vb) | 40626 | ethyl (4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyl-2-octynoate | C16H27NO5 | 详情 | 详情 | |
| (VIa) | 40627 | tert-butyl (1S)-3-methyl-1-[(2R)-5-oxotetrahydro-2-furanyl]butylcarbamate | C14H25NO4 | 详情 | 详情 | |
| (VIb) | 40628 | tert-butyl (1S)-3-methyl-1-[(2S)-5-oxotetrahydro-2-furanyl]butylcarbamate | C14H25NO4 | 详情 | 详情 | |
| (I) | 23663 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine | C11H21NO4 | 详情 | 详情 | |
| (II) | 40395 | tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-3-methylbutylcarbamate | C13H26N2O4 | 详情 | 详情 | |
| (III) | 27058 | tert-butyl (1S)-1-formyl-3-methylbutylcarbamate | C11H21NO3 | 详情 | 详情 | |
| (IV) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (VII) | 40629 | tert-butyl (1S)-3-methyl-1-[(2S,4R)-4-methyl-5-oxotetrahydro-2-furanyl]butylcarbamate | C15H27NO4 | 详情 | 详情 | |
| (VIII) | 40630 | (2R,4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-2,7-dimethyloctanoic acid | C15H29NO5 | 详情 | 详情 | |
| (IX) | 40631 | (2R,4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-[[tert-butyl(dimethyl)silyl]oxy]-2,7-dimethyloctanoic acid | C21H43NO5Si | 详情 | 详情 | |
| (X) | 40632 | (2R,4S,5S)-5-amino-4-[[tert-butyl(dimethyl)silyl]oxy]-2,7-dimethyloctanoic acid | C16H35NO3Si | 详情 | 详情 | |
| (XI) | 40633 | (2R,4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxy]-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,7-dimethyloctanoic acid | C31H45NO5Si | 详情 | 详情 |
合成路线6
该中间体在本合成路线中的序号：(IV)Boc-Leucine (I) was converted to Weinreb amide (II) by activation with isobutyl chloroformate and N-methylpiperidine, followed by treatment of the resulting mixed anhydride with N,O-dimethylhydroxylamine. Reduction of (II) with LiAlH4 provided the aldehyde (III), which was condensed with the lithium anion of ethyl propiolate (IV) to furnish the acetylenic alcohol (Va-b) as an inseparable mixture of diastereomers. Catalytic hydrogenation of the triple bond of (Va-b) over Pd/BaSO4, followed by acid-catalyzed lactonization of the resulting hydroxy ester provided the diastereomeric mixture of gamma-lactones (VIa-b). After separation by column chromatography, alkylation of the desired isomer employing iodomethane and lithium hexamethyldisilazide at -78 C provided the desired alpha-methyl lactone (VII), along with a small amount of the corresponding epimer. Lactone (VII) hydrolysis using LiOH gave hydroxy acid (VIII), which was further protected as the silyl ether (IX) with tert-butyldimethylsilyl chloride and imidazole. The Boc protecting group of (IX) was selectively removed by treatment with trifluoroacetic acid in CH2Cl2 at 0 C, and the resulting amine (X) was treated with Fmoc-succinimide to provide the Fmoc-protected intermediate (XI).
| 【1】 Lin, X.; Shin, D.; Downs, D.; Tang, J.; Koelsch, G.; Ghosh, A.K.; Ermolieff, J.; Design of potent inhibitors for human brain memapsin 2 (beta-secretase). J Am Chem Soc 2000, 122, 14, 3522. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (Va) | 40625 | ethyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyl-2-octynoate | C16H27NO5 | 详情 | 详情 | |
| (Vb) | 40626 | ethyl (4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-7-methyl-2-octynoate | C16H27NO5 | 详情 | 详情 | |
| (VIa) | 40627 | tert-butyl (1S)-3-methyl-1-[(2R)-5-oxotetrahydro-2-furanyl]butylcarbamate | C14H25NO4 | 详情 | 详情 | |
| (VIb) | 40628 | tert-butyl (1S)-3-methyl-1-[(2S)-5-oxotetrahydro-2-furanyl]butylcarbamate | C14H25NO4 | 详情 | 详情 | |
| (I) | 23663 | (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid；N-Boc-L-leucine | C11H21NO4 | 详情 | 详情 | |
| (II) | 40395 | tert-butyl (1S)-1-[[methoxy(methyl)amino]carbonyl]-3-methylbutylcarbamate | C13H26N2O4 | 详情 | 详情 | |
| (III) | 27058 | tert-butyl (1S)-1-formyl-3-methylbutylcarbamate | C11H21NO3 | 详情 | 详情 | |
| (IV) | 35333 | ethyl propiolate | 623-47-2 | C5H6O2 | 详情 | 详情 |
| (VII) | 40629 | tert-butyl (1S)-3-methyl-1-[(2S,4R)-4-methyl-5-oxotetrahydro-2-furanyl]butylcarbamate | C15H27NO4 | 详情 | 详情 | |
| (VIII) | 40630 | (2R,4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-2,7-dimethyloctanoic acid | C15H29NO5 | 详情 | 详情 | |
| (IX) | 40631 | (2R,4S,5S)-5-[(tert-butoxycarbonyl)amino]-4-[[tert-butyl(dimethyl)silyl]oxy]-2,7-dimethyloctanoic acid | C21H43NO5Si | 详情 | 详情 | |
| (X) | 40632 | (2R,4S,5S)-5-amino-4-[[tert-butyl(dimethyl)silyl]oxy]-2,7-dimethyloctanoic acid | C16H35NO3Si | 详情 | 详情 | |
| (XI) | 40633 | (2R,4S,5S)-4-[[tert-butyl(dimethyl)silyl]oxy]-5-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-2,7-dimethyloctanoic acid | C31H45NO5Si | 详情 | 详情 |