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【结 构 式】

【分子编号】17650

【品名】[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol

【CA登记号】

【 分 子 式 】C11H12ClN5O

【 分 子 量 】265.70208

【元素组成】C 49.73% H 4.55% Cl 13.34% N 26.36% O 6.02%
与该中间体有关的原料药合成路线共 15 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1

该中间体在本合成路线中的序号：(VIII)

The hydrolysis of the diacetyl derivative (I) with Ba(OH)2 in refluxing water gives the amino alcohol (II), which is condensed with 4,6-dichloro-2-aminopyrimidine (III) by means of TEA in refluxing tert-butanol to yield the adduct (IV). The condensation of (IV) with the diazonium salt (V) affords the azo compound (VI), which is reduced with Zn/HOAc to provide the diamine (VII). The cyclization of (VII) with triethyl orthoformate gives the 6-chloropurine derivative (VIII), which is finally treated with NaOH in refluxing water to afford the target guanine derivative as a racemic compound.

参考文献 中间体
合成目标
【1】 Vince, R.; Hua, M.; Synthesis and anti-HIV activity of carbocyclic 2',3'-didehydro-2',3'-dideoxy 2,6-disubstituted purine nucleosides. J Med Chem 1990, 33, 1, 17-21.
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) 45366 [(1S,4R)-4-(acetamido)-2-cyclopenten-1-yl]methyl acetate C10H15NO3 详情 详情
(II) 17647 [(1S,4R)-4-amino-2-cyclopenten-1-yl]methanol C6H11NO 详情 详情
(III) 14404 4,6-dichloro-2-pyrimidinamine; 2-Amino-4,6-dichloropyrimidine; 4,6-dichloro-2-pyrimidinylamine 56-05-3 C4H3Cl2N3 详情 详情
(IV) 17657 [(1S,4R)-4-[(2-amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H13ClN4O 详情 详情
(V) 10197 4-Chlorobenzenediazonium chloride C6H4Cl2N2 详情 详情
(VI) 17659 [(1S,4R)-4-([2-amino-6-chloro-5-[(E)-2-(4-chlorophenyl)diazenyl]-4-pyrimidinyl]amino)-2-cyclopenten-1-yl]methanol C16H16Cl2N6O 详情 详情
(VII) 17660 [(1S,4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H14ClN5O 详情 详情
(VIII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情

合成路线2

该中间体在本合成路线中的序号：(VIII)

The condensation of 6-chloropurine-2-amine (I) with epoxide (II) by means of Pd(PPh3)4 in DMSO gives the cyclopentenol derivative (III), which is treated with dimethyl dicarbonate and DMAP in dichloromethane to yield the carbonate (IV). The condensation of (IV) with ethyl 2-nitroacetate (V) by means of Pd in THF affords the adduct (VI), which is decarboxylated by means of NaCl in DMSO/water at 150 C to provide the nitromethylcyclopentene derivative (VII). The reaction of (VII) with tBuOK, O3 and NaBH4 in methanol gives the corresponding hydroxymethyl derivative (VIII), which is finally hydrolyzed with NaOH in refluxing water to afford the target guanine as a racemic compound. Alternatively, the nitromethyl-cyclopentene derivative (VII) can also be obtained by condensation of carbonate (IV) with 2-(trimethylsilyl)ethyl 2-nitroacetate (IX) by means of Pd in THF to give the adduct (X), which is decarboxylated by means of CsF in hot acetonitrile, affording (VII).

参考文献 中间体
合成目标
【1】 Peel, M.R.; et al.; A short, enantioselective synthesis of the carbocyclic nucleoside carbovir. J Org Chem 1991, 56, 16, 4990.
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) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(II) 45367 6-oxabicyclo[3.1.0]hex-2-ene C5H6O 详情 详情
(III) 45368 (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-ol C10H10ClN5O 详情 详情
(IV) 45369 (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl methyl carbonate C12H12ClN5O3 详情 详情
(V) 15050 ethyl 2-nitroacetate; Acetic acid, nitro-, ethyl ester 626-35-7 C4H7NO4 详情 详情
(VI) 45370 ethyl (2S)-2-[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]-2-nitroethanoate C14H15ClN6O4 详情 详情
(VII) 45371 6-chloro-9-[(1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl]-9H-purin-2-ylamine; 6-chloro-9-[(1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl]-9H-purin-2-amine C11H11ClN6O2 详情 详情
(VIII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(IX) 45372 2-(trimethylsilyl)ethyl 2-nitroacetate C7H15NO4Si 详情 详情
(X) 45373 2-(trimethylsilyl)ethyl (2S)-2-[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]-2-nitroethanoate C17H23ClN6O4Si 详情 详情

合成路线3

该中间体在本合成路线中的序号：(IX)

The condensation of 6-chloropurine-2-amine (III) with the chiral monoacetate (II) (obtained by enzymatic desymmetrization of diacetate (I)) by means of Pd(PPh3)4 in DMSO gives the cyclopentenol derivative (IV), which is treated with dimethyl dicarbonate and DMAP in dichloromethane to yield the carbonate (V). The condensation of (V) with ethyl 2-nitroacetate (VI) by means of Pd in THF affords the adduct (VII), which is decarboxylated by means of NaCl in DMSO/water at 150 C to provide the nitromethylcyclopentene derivative (VIII). The reaction of (VIII) with tBuOK, O3 and NaBH4 in methanol gives the corresponding hydroxymethyl derivative (IX), which is finally hydrolyzed with NaOH in refluxing water to afford the target guanine as a racemic compound. Alternatively, the nitromethyl-cyclopentene derivative (VIII) can also be obtained by condensation of carbonate (V) with 2-(trimethylsilyl)ethyl 2-nitroacetate (X) by means of Pd in THF to give the adduct (XI), which is decarboxylated by means of CsF in hot acetonitrile, affording (VIII).

参考文献 中间体
合成目标
【1】 Peel, M.R.; et al.; A short, enantioselective synthesis of the carbocyclic nucleoside carbovir. J Org Chem 1991, 56, 16, 4990.
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) 45374 (1R,4S)-4-(acetoxy)-2-cyclopenten-1-yl acetate C9H12O4 详情 详情
(II) 33169 (1S,4R)-4-hydroxy-2-cyclopenten-1-yl acetate C7H10O3 详情 详情
(III) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(IV) 45368 (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-ol C10H10ClN5O 详情 详情
(V) 45369 (1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl methyl carbonate C12H12ClN5O3 详情 详情
(VI) 15050 ethyl 2-nitroacetate; Acetic acid, nitro-, ethyl ester 626-35-7 C4H7NO4 详情 详情
(VII) 45370 ethyl (2S)-2-[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]-2-nitroethanoate C14H15ClN6O4 详情 详情
(VIII) 45371 6-chloro-9-[(1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl]-9H-purin-2-ylamine; 6-chloro-9-[(1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl]-9H-purin-2-amine C11H11ClN6O2 详情 详情
(IX) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(X) 45372 2-(trimethylsilyl)ethyl 2-nitroacetate C7H15NO4Si 详情 详情
(XI) 45373 2-(trimethylsilyl)ethyl (2S)-2-[(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]-2-nitroethanoate C17H23ClN6O4Si 详情 详情

合成路线4

该中间体在本合成路线中的序号：(XII)

The hydrolysis of the chiral unsaturated bicyclic lactam (I) with aqueous refluxing HCl gives the amino acid (II), which is esterified with 2,2-dimethoxypropane, methanol and HCl to yield the methyl ester (III). The acylation of (III) with Ac2O and pyridine in dichloromethane affords the acetamide (IV), which is reduced with calcium borohydride in THF, providing the carbinol (V). The hydrolysis of the amido group of (V) with HCl in refluxing ethanol/water gives the chiral amino alcohol (VI), which is condensed with 2-amino-4,6-dichloropyrimidine (VII) by means of DIEA in refluxing butanol, yielding the adduct (VIII). The reaction of (VIII) with 4-chlorophenyldiazonium chloride (IX) by means of HOAc and NaOAc in water affords the azo compound (X), which is reduced with Zn and HOAc to provide the triaminopyrimidine (XI). The cyclization of (XI) with triethyl orthoformate gives the carbocyclic chloropurine (XII), which is finally treated with NaOH in refluxing water to yield the target carbocyclic guanine.

参考文献 中间体
合成目标
【1】 Evans, C.T.; et al.; Potential use of carbocyclic nucleosides for the treatment of AIDS - Chemo-enzymatic syntheses of the enantiomers of carbovir. J Chem Soc - Perkins Trans I 1992, 5, 589.
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) 33410 cis-2-azabicyclo[2.2.1]hept-5-en-3-one C6H7NO 详情 详情
(II) 33411 cis-4-amino-2-cyclopentene-1-carboxylic acid 168471-40-7 C6H9NO2 详情 详情
(III) 33412 methyl cis-4-amino-2-cyclopentene-1-carboxylate C7H11NO2 详情 详情
(IV) 45391 methyl (1S,4R)-4-(acetamido)-2-cyclopentene-1-carboxylate C9H13NO3 详情 详情
(V) 45392 N-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]acetamide 130931-86-1 C8H13NO2 详情 详情
(VI) 17647 [(1S,4R)-4-amino-2-cyclopenten-1-yl]methanol C6H11NO 详情 详情
(VII) 14404 4,6-dichloro-2-pyrimidinamine; 2-Amino-4,6-dichloropyrimidine; 4,6-dichloro-2-pyrimidinylamine 56-05-3 C4H3Cl2N3 详情 详情
(VIII) 17657 [(1S,4R)-4-[(2-amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H13ClN4O 详情 详情
(IX) 10197 4-Chlorobenzenediazonium chloride C6H4Cl2N2 详情 详情
(X) 17659 [(1S,4R)-4-([2-amino-6-chloro-5-[(E)-2-(4-chlorophenyl)diazenyl]-4-pyrimidinyl]amino)-2-cyclopenten-1-yl]methanol C16H16Cl2N6O 详情 详情
(XI) 17660 [(1S,4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H14ClN5O 详情 详情
(XII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情

合成路线5

该中间体在本合成路线中的序号：(IX)

The epoxidation of 3-cyclopentene-1-carboxylic acid methyl ester (I) with MCPBA in cyclohexane gives the trans-epoxide (II) along with some cis-isomer that is separated by chromatography. The reduction of the ester group of (II) with LiAlH4 in ether yields the corresponding trans-carbinol (III), which is silylated with Tbdms-Cl and imidazole to afford the silyl ether (IV). The reaction of the epoxide (IV) with the chiral lithium pyrrolidide (V) in benzene provides the (1S,3S)(trans) 3-(tertbutyldimethylsilyloxy)-4-cyclopenten-1-ol (VI). The condensation of (VI) with 2-amino-6-chloropurine by means of diethyl azodicarboxylate (DEAD) and PPh3 in dioxane gives the carbocyclic purine derivative (VIII), which is desilylated by means of TBAF in THF to the chloropurine (IX). Finally, this compound is hydrolyzed with refluxing aqueous NaOH to yield the target carbocyclic guanine.

参考文献 中间体
合成目标
【1】 Asami, M.; Inoue, S.; Takahashi, J.; An asymmetric synthesis of (-)-carbovir. Tetrahedron Asymmetry 1994, 5, 9, 1649.
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) 45412 methyl 3-cyclopentene-1-carboxylate C7H10O2 详情 详情
(II) 45413 methyl (1R,5S)-6-oxabicyclo[3.1.0]hexane-3-carboxylate C7H10O3 详情 详情
(III) 45414 (1R,5S)-6-oxabicyclo[3.1.0]hex-3-ylmethanol C6H10O2 详情 详情
(IV) 45415 tert-butyl(dimethyl)[(1R,5S)-6-oxabicyclo[3.1.0]hex-3-ylmethoxy]silane; tert-butyl(dimethyl)silyl (1R,5S)-6-oxabicyclo[3.1.0]hex-3-ylmethyl ether C12H24O2Si 详情 详情
(V) 45416 　 C9H17LiN2 详情 详情
(VI) 45417 (1S,4S)-4-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-cyclopenten-1-ol 886-65-7 C12H24O2Si 详情 详情
(VII) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(VIII) 45418 9-[(1R,4S)-4-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-cyclopenten-1-yl]-6-chloro-9H-purin-2-ylamine; 9-[(1R,4S)-4-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-cyclopenten-1-yl]-6-chloro-9H-purin-2-amine C17H26ClN5OSi 详情 详情
(IX) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情

合成路线6

该中间体在本合成路线中的序号：(XIII)

The condensation of the chiral oxazolidinone (I) with the pentenoic anhydride (II) by means of n-BuLi in THF gives the N-pentenoyloxazolidinone (III), which is condensed with acrolein (IV) catalyzed by TiCl4 and (-)-spartein in dichloromethane, yielding the chiral adduct (V). The ring-closing metathesis of (V) by means of a Ru catalyst in dichloromethane affords the chiral cyclopentenol derivative (VI), which is reduced to the (R,R)-5-(hydroxymethyl)-2-cyclopenten-1-ol (VII) by means of LiBH4 in THF. The reaction of diol (VII) with Ac2O; with methyl chloroformate, TEA and DMAP; or with ethyl chloroformate and pyridine gives the diacetate (VIII), the cyclic carbonate (IX) or the dicarbonate (X), respectively. The condensation of (VIII), (IX) or (X) with 2-amino-6-chloropurine (XI) by means of Pd(PPh3)4 yields the carbocyclic purines (XII), (XIII) or (XIV), respectively. Finally, these compounds are hydrolyzed with aqueous NaOH to the target carbocyclic guanine.

参考文献 中间体
合成目标
【1】 Crimmins, M.T.; et al.; An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy. J Org Chem 2000, 65, 25, 8499.
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) 14694 (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone 90719-32-7 C10H11NO2 详情 详情
(II) 17666 1,1-dimethylpropionic 4-pentenoic anhydride C10H16O3 详情 详情
(III) 17667 (4S)-4-benzyl-3-(4-pentenoyl)-1,3-oxazolidin-2-one C15H17NO3 详情 详情
(IV) 17668 acrylaldehyde; Acrolein 107-02-8 C3H4O 详情 详情
(V) 17669 (4S)-3-[(2S,3R)-2-allyl-3-hydroxy-4-pentenoyl]-4-benzyl-1,3-oxazolidin-2-one C18H21NO4 详情 详情
(VI) 17670 (4S)-4-benzyl-3-[[(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]carbonyl]-1,3-oxazolidin-2-one C16H17NO4 详情 详情
(VII) 17671 (1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol C6H10O2 详情 详情
(VIII) 17674 [(1R,2R)-2-(acetoxy)-3-cyclopenten-1-yl]methyl acetate C10H14O4 详情 详情
(IX) 17673 (4aR,7aR)-4,4a,5,7a-tetrahydrocyclopenta[d][1,3]dioxin-2-one C7H8O3 详情 详情
(X) 17672 [(1R,2R)-2-[(methoxycarbonyl)oxy]-3-cyclopenten-1-yl]methyl methyl carbonate C10H14O6 详情 详情
(XI) 11664 4-Chloro-3-nitroquinoline C9H5ClN2O2 详情 详情
(XII) 45424 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl acetate C13H14ClN5O2 详情 详情
(XIII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(XIV) 45398 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl methyl carbonate C13H14ClN5O3 详情 详情

合成路线7

该中间体在本合成路线中的序号：(V)

The reaction of 14C-labeled cyanhydric acid (I) with HCl and ethanol gives the iminoester (II), which by reaction with more ethanol in chloroform yields the labeled orthoester (III). The cyclization of the triaminopyrimidinone (IV) with orthoester (III) by means of Ms-OH in chloroform affords the chloropurine derivative (V), which is finally hydrolyzed with NaOH to afford the target compound, the 14C-labeled carbovir.

参考文献 中间体
合成目标
【1】 Gopinathan, M.B.; Kepler, J.A.; Synthesis of carbon-14 labelled cis-2-amino-1,9-dihydro-9-[4-(hydroxymethyl)-2-cyclopenten-1-yl]-H6-purine-6-one; [8-14C]carbovir: A promising anti-AIDS drug. J Label Compd Radiopharm 1991, 29, 6, 645.
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) 55517 nitrilomethane CHN 详情 详情
(I) 55518 nitrilomethane CHN 详情 详情
(II) 13213 ethyl iminoformate C3H7NO 详情 详情
(II) 55519 ethyl iminoformate C3H7NO 详情 详情
(III) 27311 trimethoxymethane;Trimethyl orthoformate;Methyl orthoformate 149-73-5 C4H10O3 详情 详情
(III) 55520 trimethoxymethane; dimethoxymethyl methyl ether C4H10O3 详情 详情
(IV) 17660 [(1S,4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H14ClN5O 详情 详情
(V) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(V) 55521 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情

合成路线8

该中间体在本合成路线中的序号：(VIII)

The reaction of 2-azabicyclo[2,2,1]-5-hepten-3-one (I) with 2-nitrophenylsulfonyl chloride (II) by means of BuLi in THF gives the sulfonamide (III), which is condensed with the chloropurine (IV) by means of Pd[P(OPr)3]4 in THF or NMP to yield the adduct (V). The N-protection of the formamide group of (V) with Boc2O and NaH in THF affords compound (VI), which is reduced and deprotected with NaBH4 in methanol to provide the N-Boc protected chloropurine (VII). Finally, this compound is treated with hot HOAc to furnish the target chloropurine (VIII) (see schemes 14673102a intermediate (VIII), 14673103a intermediate (VIII), 14673104a intermediate (IX), 14673107a intermediate (XII), 14673111a intermediate (IX) and 14673113a intermediate (XIII)).

参考文献 中间体
合成目标
【1】 katagiri, N.; et al.; Efficient synthesis of carbovir and its congener via pi-allylpalladium complex formation by ring strain-assisted C-N bond cleavage. J Org Chem 1997, 62, 6, 1580.
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) 55527 2-azabicyclo[2.2.1]hept-5-en-3-one C6H7NO 详情 详情
(II) 32624 2-Nitrobenzenesulfonyl chloride 1694-92-4 C6H4ClNO4S 详情 详情
(III) 55522 2-[(2-nitrophenyl)sulfonyl]-2-azabicyclo[2.2.1]hept-5-en-3-one C12H10N2O5S 详情 详情
(IV) 55523 6-chloro-9H-purin-2-ylformamide C6H4ClN5O 详情 详情
(V) 55524 N-({(1S,4R)-4-[6-chloro-2-(formylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl}carbonyl)-2-nitrobenzenesulfonamide C18H14ClN7O6S 详情 详情
(VI) 55525 tert-butyl 6-chloro-9-[(1R,4S)-4-({[(2-nitrophenyl)sulfonyl]amino}carbonyl)-2-cyclopenten-1-yl]-9H-purin-2-yl(formyl)carbamate C23H22ClN7O8S 详情 详情
(VII) 55526 tert-butyl 6-chloro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purin-2-ylcarbamate C16H20ClN5O3 详情 详情
(VIII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情

合成路线9

该中间体在本合成路线中的序号：(XI)

The reaction of the commercially available (1S-cis)-2-cyclopentan-1,4-diol 4-acetate (I) with methyl pyrocarbonate and DMAP in THF gives the carbonate ester (II), which by reaction with nitromethane (III), triisopropyl phosphite and a Pd catalyst, yields (1R-cis)-1-acetoxy-4-(nitromethyl)-2-cyclopentene (IV). The hydrolysis of (IV) by means of Ts-OH in methanol affords the corresponding alcohol (V), which by treatment with O3, NaOMe and NaBH4 in methanol provides (1R-cis)-4-(hydroxymethyl)-2-cyclopenten-1-ol (VI). The selective monotritylation of the primary OH group of (VI) with trityl chloride (VII) in pyridine gives the trityl ether (VIII), which is condensed with 2-amino-6-chloropurine (IX) by means of Pd(PPh3)4 in THF to yield the adduct (X). The destritylation of (X) with HOAc/water affords the hydroxymethyl compound (XI), which is finally dechlorinated by hydrolysis with hot HCl or NaOH to provide the target (-)-carbovir. Alternatively, the dechlorination of (XI) can be performed by reaction of (XI) with liquid ammonia at 75-80 C in a Parr bomb to give the diaminopurine (XII), which is finally submitted to an enzymatic deamination with adenosine deaminase (from calf intestinal mucosa).

参考文献 中间体
合成目标
【1】 Vince, R.; Peterson, M.L.; Lackey, J.W.; Mook, R.A. Jr.; Partridge, J.J. (GlaxoSmithKline plc); Synthesis of purine substd. cyclopentene derivs.. US 5126452 .
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) 45407 (1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate; (1S,4R)-4-acetoxy-2-cyclopentenol 60410-16-4 C7H10O3 详情 详情
(II) 55528 (1R,4S)-4-[(methoxycarbonyl)oxy]-2-cyclopenten-1-yl acetate C9H12O5 详情 详情
(III) 39563 nitromethane 75-52-5 CH3NO2 详情 详情
(IV) 55529 (1R,4S)-4-(nitromethyl)-2-cyclopenten-1-yl acetate C8H11NO4 详情 详情
(V) 55530 (1R,4S)-4-(nitromethyl)-2-cyclopenten-1-ol C6H9NO3 详情 详情
(VI) 45405 (1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-ol C6H10O2 详情 详情
(VII) 28630 Triphenylchloromethane; 1-[Chloro(diphenyl)methyl]benzene; Trityl chloride 76-83-5 C19H15Cl 详情 详情
(VIII) 55531 (1R,4S)-4-[(trityloxy)methyl]-2-cyclopenten-1-ol C25H24O2 详情 详情
(IX) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(X) 55532 6-chloro-9-{(1R,4S)-4-[(trityloxy)methyl]-2-cyclopenten-1-yl}-9H-purin-2-amine; 6-chloro-9-{(1R,4S)-4-[(trityloxy)methyl]-2-cyclopenten-1-yl}-9H-purin-2-ylamine C30H26ClN5O 详情 详情
(XI) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(XII) 55533 [(1S,4R)-4-(2,6-diamino-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H14N6O 详情 详情

合成路线10

该中间体在本合成路线中的序号：(XI)

The cyclization of glyoxylic acid (I) with cyclopentadiene (II) gives the racemic hydroxylactone (III), which is acylated with Ac2O to yield acetoxy compound (rac)-(IV). The enzymatic optical resolution of (rac)-(IV) by means of Pseudomonas fluorescens affords the chiral hydroxylactone (-)-(V), which is reduced with LiAlH4 in refluxing THF to provide the lactol (VI). The oxidation of (VI) with NaIO4 in ethyl ether/water gives the chiral carbaldehyde (VII), which is reduced with NaBH4 in ethanol to afford the diol (VIII). The reaction of (VIII) with triphosgene by means of TEA in dichloromethane affords the cyclic carbonate (IX), which is condensed with chloropurine (X) by means of Pd(PPh3)4 in DMSO/THF to provide the adduct (XI). Finally, this compound is hydrolyzed with NaOH to afford the target (-)-carbovir.

参考文献 中间体
合成目标
【1】 Yu, J.; Olivo, H.F.; Practical enantiodivergent syntheses of both enantiomers of carbovir, 1592U89 and six-membered ring analogues. J Chem Soc - Perkins Trans I 1998, 3, 3, 391-2.
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) 15618 2-Oxoacetic acid; Glyoxylic Acid 298-12-4 C2H2O3 详情 详情
(II) 11183 1,3-Cyclopentadiene C5H6 详情 详情
(III) 55545 (3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one C7H8O3 详情 详情
(IV) 17679 (3S,3aR,6aR)-2-oxo-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-3-yl acetate C9H10O4 详情 详情
(V) 17678 (3S,3aR,6aR)-3-hydroxy-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one C7H8O3 详情 详情
(VI) 55544 (3S,3aR,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2,3-diol C7H10O3 详情 详情
(VII) 17682 (1S,2R)-2-hydroxy-3-cyclopentene-1-carbaldehyde C6H8O2 详情 详情
(VIII) 17671 (1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol C6H10O2 详情 详情
(IX) 17673 (4aR,7aR)-4,4a,5,7a-tetrahydrocyclopenta[d][1,3]dioxin-2-one C7H8O3 详情 详情
(X) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(XI) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情

合成路线11

该中间体在本合成路线中的序号：(IX)

1) The reaction of 4,6-dihydroxypyrimidine-2,5-diamine (I) with (chloromethylene)dimethylammonium chloride (II) in refluxing chloroform gives 4,6-dichloro-2,5-bis(dimethylaminomethyleneamino)pyrimidine (III), which by reaction with aqueous HCl in hot ethanol yields monoamine (IV). The reaction of (IV) with a refluxing phosphate buffer (pH 3.2) affords N-(2-amino-4,6-dichloropyrimidin-5-yl)formamide (V). The condensation of (V) with (1S,4R)-4-amino-2-cyclopentene-1-methanol (VI) (which was obtained by optical resolution of the cis-racemate (VII) with D-dibenzoyltartaric acid, and elimination of the acid with ion exchange resin Amberlite IA-400, by means of triethylamine and NaOH in refluxing ethanol) gives N-[2-amino-4-chloro-6-[4(S)-(hydroxymethyl)-2-cyclopenten-1(R)-ylamino]pyrimidin-5-yl]formamide (VIII). The cyclization of (VIII) with refluxing diethoxymethyl acetate or triethyl orthoformate yields the corresponding purine derivative (IX), which is finally treated with cyclopropylamine (X) in refluxing n-butanol. 2) The formylation of N-(5-amino-4,6-dichloropyrimidin-2-yl)acetamide (XI) with 95% formic acid in acetic anhydride gives the expected formamide (XII), which is condensed with (1S,4R)-4-amino-2-cyclopentene-1-methanol (VI) by means of triethylamine in hot ethanol to yield the substituted pyrimidine (XIII). Finally, the cyclization of (XIII) with diethoxymethyl acetate as before affords the purine intermediate (IX).

参考文献 中间体
合成目标
【1】 Graul, A.; Castaner, J.; Leeson, P.A.; Abacavir Sulfate. Drugs Fut 1998, 23, 11, 1155-1167.
【2】 Daluge, S.M. (Glaxo Wellcome plc); Therapeutic nucleosides. EP 0434450; JP 1996092252; JP 1999158160; JP 1999343292 .
【3】 Daluge, S.M. (Glaxo Wellcome plc); Therapeutic nucleosides. AU 8937025; EP 0349242; JP 1990045486; JP 1999139976; US 5034394; US 5089500 .
【4】 Daluge, S.M.; Martin, M.T.; Fugett, M.J.F.; Chloropyrimide intermediates. WO 9521161 .
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) 17642 2,5-diamino-4,6-pyrimidinediol C4H6N4O2 详情 详情
(II) 17643 (Chloromethylene)dimethylammonium chloride; N-(chloromethylene)-N-methylmethanaminium chloride 3724-43-4 C3H7Cl2N 详情 详情
(III) 17644 N'-(4,6-dichloro-2-[[(E)-(dimethylamino)methylidene]amino]-5-pyrimidinyl)-N,N-dimethyliminoformamide C10H14Cl2N6 详情 详情
(IV) 17645 N'-(2-amino-4,6-dichloro-5-pyrimidinyl)-N,N-dimethyliminoformamide C7H9Cl2N5 详情 详情
(V) 17646 2-amino-4,6-dichloro-5-pyrimidinylformamide C5H4Cl2N4O 详情 详情
(VI) 17647 [(1S,4R)-4-amino-2-cyclopenten-1-yl]methanol C6H11NO 详情 详情
(VII) 63843 (rac)-[(1R*,4S*)-4-amino-2-cyclopenten-1-yl]methanol C6H11NO 详情 详情
(VIII) 17649 2-amino-4-chloro-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-5-pyrimidinylformamide C11H14ClN5O2 详情 详情
(IX) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(X) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
(XI) 17652 N-(5-amino-4,6-dichloro-2-pyrimidinyl)acetamide C6H6Cl2N4O 详情 详情
(XII) 17653 N-[4,6-dichloro-5-(formylamino)-2-pyrimidinyl]acetamide C7H6Cl2N4O2 详情 详情
(XIII) 17654 N-(4-chloro-5-(formylamino)-6-[[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]amino]-2-pyrimidinyl)acetamide C13H16ClN5O3 详情 详情

合成路线12

该中间体在本合成路线中的序号：(XXI)

3) The condensation of (±)-cis-4-acetamido-2-cyclopentenylmethyl acetate (XIV) with 2-amino-4,6-dichloropyrimidine (XV) by means of Ba(OH)2 and triethylamine in refluxing butanol gives the expected condensation product (XVI), which is treated with 4-chlorophenyldiazonium chloride (XVII) in water/acetic acid to yield the corresponding azo-compound (XVIII). The reduction of (XVIII) with Zn/acetic acid in ethanol affords the diamine (XIX), which is cyclized with refluxing diethoxymethyl acetate (XX) to afford the corresponding purine (XXI). The reaction of (XXI) with cyclopropylamine (X) in refluxing ethanol affords racemic abacavir (XXII), which is phosphorylated with POCl3 giving the racemic 4'-O-phosphate (XXIII). Finally, this compound is submitted to stereoselective enzymatic dephosphorylation using snake venom 5'-nucleotidase (EC 3.1.3.5) from Crotalus atrox yielding the (-)-enantiomer, abacavir.

参考文献 中间体
合成目标
【1】 Graul, A.; Castaner, J.; Leeson, P.A.; Abacavir Sulfate. Drugs Fut 1998, 23, 11, 1155-1167.
【2】 Daluge, S.M. (Glaxo Wellcome plc); Therapeutic nucleosides. EP 0434450; JP 1996092252; JP 1999158160; JP 1999343292 .
【3】 Daluge, S.M. (Glaxo Wellcome plc); Therapeutic nucleosides. AU 8937025; EP 0349242; JP 1990045486; JP 1999139976; US 5034394; US 5089500 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(X) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
(XIV) 17655 (1S,4R)-4-(acetamido)-2-cyclopenten-1-yl acetate C9H13NO3 详情 详情
(XV) 14404 4,6-dichloro-2-pyrimidinamine; 2-Amino-4,6-dichloropyrimidine; 4,6-dichloro-2-pyrimidinylamine 56-05-3 C4H3Cl2N3 详情 详情
(XVI) 17657 [(1S,4R)-4-[(2-amino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H13ClN4O 详情 详情
(XVII) 10197 4-Chlorobenzenediazonium chloride C6H4Cl2N2 详情 详情
(XVIII) 17659 [(1S,4R)-4-([2-amino-6-chloro-5-[(E)-2-(4-chlorophenyl)diazenyl]-4-pyrimidinyl]amino)-2-cyclopenten-1-yl]methanol C16H16Cl2N6O 详情 详情
(XIX) 17660 [(1S,4R)-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopenten-1-yl]methanol C10H14ClN5O 详情 详情
(XX) 17661 Diethoxymethyl acetate 14036-06-7 C7H14O4 详情 详情
(XXI) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(XXII) 17663 [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl]methanol C14H18N6O 详情 详情
(XXIII) 17664 [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl dihydrogen phosphate C14H19N6O4P 详情 详情

合成路线13

该中间体在本合成路线中的序号：(IX)

4) The acylation of 4(S)-benzyloxazolidin-2-one (XXIV) with 4-pentenoyl pivaloyl anhydride (XXV) by means of NaH in THF gives 4(S)-benzyl-3-(4-pentenoyl)oxazolidin-2-one (XXVI), which is submitted to a diastereoselective syn aldol condensation with acrolein (XXVII), using dibutylboron triflate as catalyst, affording the aldol (XXVIII). The cyclization of (XXVIII) by means of the Grubbs catalyst in dichloromethane yields the cyclopentenol (XXIX), which is reduced with LiBH4 in THF/methanol to give the key intermediate 5(R)-(hydroxymethyl)-2-cyclopenten-1(R)-ol (XXX). The reaction of (XXX) with methyl chloroformate/pyridine/DMAP or methyl chloroformate/triethylamine/DMAP or acetic anhydride gives the diols (XXXI), (XXXII) and (XXXIII), respectively, each of which coupled with 2-amino-6-chloropurine (XXXIV) in the presence of NaH and palladium tetrakis(triphenylphosphine) in THF/DMSO, affords the purine intermediate (IX) already reported.

参考文献 中间体
合成目标
【1】 King, B.W.; Crimmins, M.T.; An efficient asymmetric approach to carbocyclic nucleosides: Asymmetric synthesis of 1592U89, a potent inhibitor of HIV reverse transcriptase. J Org Chem 1996, 61, 13, 4192-3.
【2】 Graul, A.; Castaner, J.; Leeson, P.A.; Abacavir Sulfate. Drugs Fut 1998, 23, 11, 1155-1167.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IX) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(XXIV) 14694 (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone 90719-32-7 C10H11NO2 详情 详情
(XXV) 17666 1,1-dimethylpropionic 4-pentenoic anhydride C10H16O3 详情 详情
(XXVI) 17667 (4S)-4-benzyl-3-(4-pentenoyl)-1,3-oxazolidin-2-one C15H17NO3 详情 详情
(XXVII) 17668 acrylaldehyde; Acrolein 107-02-8 C3H4O 详情 详情
(XXVIII) 17669 (4S)-3-[(2S,3R)-2-allyl-3-hydroxy-4-pentenoyl]-4-benzyl-1,3-oxazolidin-2-one C18H21NO4 详情 详情
(XXIX) 17670 (4S)-4-benzyl-3-[[(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]carbonyl]-1,3-oxazolidin-2-one C16H17NO4 详情 详情
(XXX) 17671 (1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol C6H10O2 详情 详情
(XXXI) 17672 [(1R,2R)-2-[(methoxycarbonyl)oxy]-3-cyclopenten-1-yl]methyl methyl carbonate C10H14O6 详情 详情
(XXXII) 17673 (4aR,7aR)-4,4a,5,7a-tetrahydrocyclopenta[d][1,3]dioxin-2-one C7H8O3 详情 详情
(XXXIII) 17674 [(1R,2R)-2-(acetoxy)-3-cyclopenten-1-yl]methyl acetate C10H14O4 详情 详情
(XXXIV) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情

合成路线14

该中间体在本合成路线中的序号：(XII)

A new solid phase synthesis of abacavir has been reported: Condensation of the chiral 4(R)-benzyl-3-(4-pentenoyl)oxazolidin-2-thione (I) with acrolein (II) by means of TiCl4 and DIEA gives the adduct (III), which was transformed into the chiral cyclopentene (IV) by catalytic ring-closing metathesis. The reductive removal of the chiral auxiliary with LiBH4 affords the chiral diol (V), which is selectively silylated with TBDMSCl providing the primary silyl ether (VI). Acylation of the secondary alcohol of (VI) with benzoic anhydride gives the benzoate (VII), which is desilylated with HF in acetonitrile yielding the allylic benzoate (VIII). Benzoate (VIII) is condensed with a p-nitrophenyl Wang carbonate resin (IX) by means of DIEA and DMAP affording the solid phase resin (X) which is condensed with 2-amino-6-chloropurine (XI) by means of a Pd catalyst furnishing the adduct (XII). Thermal condensation of (XII) with cyclopropylamine (XIII) yields the diaminopurine resin (XIV) which, after cleavage from the resin by a treatment with TFA in dichloromethane, gives directly abacavir.

参考文献 中间体
合成目标
【1】 Zuercher, W.J.; Crimmins, M.T.; Solid-phase synthesis of carbocyclic nucleosides. Org Lett 2000, 2, 8, 1065.
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) 41704 1-[(4R)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl]-4-penten-1-one C15H17NO2S 详情 详情
(II) 17668 acrylaldehyde; Acrolein 107-02-8 C3H4O 详情 详情
(III) 41705 (2S,3R)-2-allyl-1-[(4R)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl]-3-hydroxy-4-penten-1-one C18H21NO3S 详情 详情
(IV) 41706 [(4R)-4-benzyl-2-thioxo-1,3-oxazolidin-3-yl][(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]methanone C16H17NO3S 详情 详情
(V) 17671 (1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol C6H10O2 详情 详情
(VI) 41707 (1R,5R)-5-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-cyclopenten-1-ol C12H24O2Si 详情 详情
(VII) 41708 (1R,5R)-5-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-cyclopenten-1-yl benzoate C19H28O3Si 详情 详情
(VIII) 41709 (1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-yl benzoate C13H14O3 详情 详情
(XI) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(XII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(XIII) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情

合成路线15

该中间体在本合成路线中的序号：(XIII)

An efficient asymmetric synthesis of abacavir has been reported: Acylation of the chiral oxazolidinone (I) with the mixed anhydride (II) by means of BuLi in THF gives the N-pentenoyloxazolidinone (III), which by condensation with acrolein (IV) catalyzed by TiCl4 and (­)-spartein in dichloromethane yields the chiral adduct (V). The ring-closing metathesis of adduct (V) by means of the ruthenium catalyst (Cy3P)Cl2Ru=CHPh in dichloromethane affords the chiral cyclopentenol (VI), which is reduced to 5(R)-(hydroxymethyl)-2-cyclopenten-1(R)-ol (VII) by means of LiBH4 in THF. Reaction of diol (VII) with a) Ac2O, TEA and DMAP, b) methyl chloroformate, TEA and DMAP or c) methyl chloroformate, pyridine and DMAP gives a) the diacetate (VIII), b) the cyclic carbonate (IX) or c) the dicarbonate (X), respectively. The condensation of diacetate (VIII), cyclic carbonate (IX) or dicarbonate (X) with 2-amino-6-chloropurine (XI) by means of Pd(PPh3)4 yields the carbocyclic purines (XII), (XIII) or (XIV), respectively. Treatment of these chloro-purines (XII), (XIII) and (XIV) with cyclopropylamine (XV) in hot DMSO provides the corresponding cyclopropylaminopurine carbonate (XVI), abacavir or cyclopropylaminopurine acetate (XVII), respectively. Finally, the protecting groups of purines (XVI) and (XVII) are hydrolyzed with aqueous NaOH.

参考文献 中间体
合成目标
【1】 Crimmins, M.T.; et al.; An efficient, general asymmetric synthesis of carbocyclic nucleosides: Application of an asymmetric aldol/ring-closing metathesis strategy. J Org Chem 2000, 65, 25, 8499.
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) 14694 (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone 90719-32-7 C10H11NO2 详情 详情
(II) 17666 1,1-dimethylpropionic 4-pentenoic anhydride C10H16O3 详情 详情
(III) 17667 (4S)-4-benzyl-3-(4-pentenoyl)-1,3-oxazolidin-2-one C15H17NO3 详情 详情
(IV) 17668 acrylaldehyde; Acrolein 107-02-8 C3H4O 详情 详情
(V) 17669 (4S)-3-[(2S,3R)-2-allyl-3-hydroxy-4-pentenoyl]-4-benzyl-1,3-oxazolidin-2-one C18H21NO4 详情 详情
(VI) 17670 (4S)-4-benzyl-3-[[(1S,2R)-2-hydroxy-3-cyclopenten-1-yl]carbonyl]-1,3-oxazolidin-2-one C16H17NO4 详情 详情
(VII) 17671 (1R,5R)-5-(hydroxymethyl)-2-cyclopenten-1-ol C6H10O2 详情 详情
(VIII) 17674 [(1R,2R)-2-(acetoxy)-3-cyclopenten-1-yl]methyl acetate C10H14O4 详情 详情
(IX) 17673 (4aR,7aR)-4,4a,5,7a-tetrahydrocyclopenta[d][1,3]dioxin-2-one C7H8O3 详情 详情
(X) 17672 [(1R,2R)-2-[(methoxycarbonyl)oxy]-3-cyclopenten-1-yl]methyl methyl carbonate C10H14O6 详情 详情
(XI) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(XII) 45424 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl acetate C13H14ClN5O2 详情 详情
(XIII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
(XIV) 45398 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methyl methyl carbonate C13H14ClN5O3 详情 详情
(XV) 12263 Cyclopropylamine; Cyclopropanamine 765-30-0 C3H7N 详情 详情
(XVI) 49433 [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl acetate C16H20N6O2 详情 详情
(XVII) 49434 [(1S,4R)-4-[2-amino-6-(cyclopropylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl]methyl methyl carbonate C16H20N6O3 详情 详情
Extended Information