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【结 构 式】

【分子编号】14408

【品名】[(1R,2S,4S)-2-[[(cyclohexylcarbonyl)oxy]methyl]-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]cyclobutyl]methyl cyclohexanecarboxylate

【CA登记号】

【 分 子 式 】C24H36ClN5O4

【 分 子 量 】494.03384

【元素组成】C 58.35% H 7.34% Cl 7.18% N 14.18% O 12.95%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(XXXVII)

4) The reaction of the previously described chiral cyclobutanone (IX) with hydroxylamine gives the corresponding oxime (XXXI), which is reduced with H2 over PtO2 yielding [1R-(1alpha,2beta,3alpha)]-2,3-di(cyclohexylcarbonyloxymethyl) cyclobutane-1-amine (XXXII). The condensation of (XXXII) with 4,6-dichloropyrimidine-2-amine (XXXIII) affords (XXXIV), which is further condensed with 4-chlorophenyldiazonium chloride (XXXV) to give the 5-azo-pyrimidine derivative (XXXVI). The hydrogenation of the azo group of (XXXVI) with Zn/HCl yields the 2,5-diaminopyrimidine derivative (XXXVII), which is cyclized with triethyl orthoformate to afford [1R-(1alpha,2beta,3alpha)]-2-amino-9-[2,3-bis (cyclohexylcarbonyloxymethyl)cyclobutyl]-6-chloropurine (XXXVIII). Finally, this compound is converted into the final product in the usual way.

1 Ireland, C.; Leeson, P.A.; Castaner, J.; Lobucavir. Drugs Fut 1997, 22, 4, 359.
2 Honjo, M.; Maruyama, T.; Sato, Y. (Nippon Kayaku Co., Ltd.); Production of carboxetanocin G or A and intermediates therefor. WO 9110665 .
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) 14380 [(1S,2S)-2-[(benzoyloxy)methyl]-4-oxocyclobutyl]methyl benzoate C20H18O5 详情 详情
(XXXI) 14402 [(1S,2R)-2-[(benzoyloxy)methyl]-3-(hydroxyimino)cyclobutyl]methyl benzoate C20H19NO5 详情 详情
(XXXII) 14403 ((1S,2R,3R)-3-amino-2-[[(cyclohexylcarbonyl)oxy]methyl]cyclobutyl)methyl cyclohexanecarboxylate C20H33NO4 详情 详情
(XXXIII) 14404 4,6-dichloro-2-pyrimidinamine; 2-Amino-4,6-dichloropyrimidine; 4,6-dichloro-2-pyrimidinylamine 56-05-3 C4H3Cl2N3 详情 详情
(XXXIV) 14405 ((1S,2R,3R)-3-[(2-amino-6-chloro-4-pyrimidinyl)amino]-2-[[(cyclohexylcarbonyl)oxy]methyl]cyclobutyl)methyl cyclohexanecarboxylate C24H35ClN4O4 详情 详情
(XXXV) 10197 4-Chlorobenzenediazonium chloride C6H4Cl2N2 详情 详情
(XXXVI) 14407 ((1S,2R,3R)-3-([2-amino-6-chloro-5-[(E)-2-(4-chlorophenyl)diazenyl]-4-pyrimidinyl]amino)-2-[[(cyclohexylcarbonyl)oxy]methyl]cyclobutyl)methyl cyclohexanecarboxylate C30H38Cl2N6O4 详情 详情
(XXXVII) 14408 [(1R,2S,4S)-2-[[(cyclohexylcarbonyl)oxy]methyl]-4-[(2,5-diamino-6-chloro-4-pyrimidinyl)amino]cyclobutyl]methyl cyclohexanecarboxylate C24H36ClN5O4 详情 详情
(XXXVIII) 14409 ((1S,2R,3R)-3-(2-amino-6-chloro-9H-purin-9-yl)-2-[[(cyclohexylcarbonyl)oxy]methyl]cyclobutyl)methyl cyclohexanecarboxylate C25H34ClN5O4 详情 详情
Extended Information