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【结 构 式】

【分子编号】50069

【品名】4-[(1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-([[4-(allyloxy)-2,2-dimethyl-4-oxobutanoyl]oxy]methyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-9-yl] 1-allyl 2,2-dimethylsuccinate

【CA登记号】

【 分 子 式 】C48H74O8

【 分 子 量 】779.11076

【元素组成】C 74% H 9.57% O 16.43%

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:(IX)

Reaction of betulin (I) and 2,2-dimethylsuccinic acid (II) in refluxing pyridine, followed by HPLC separation of the two products obtained, affords derivative (III). Protection of the carboxylic group of (III) is then performed by formation of the corresponding allyl ester derivative (V) by reaction with allyl bromide (IV) and K2CO3 in acetone. Separately, 2,2-dimethylsuccinic acid (II) is treated with allyl alcohol (VI) in refluxing pyridine to give an isomeric mixture of compounds from which allyl succinate derivative (VII) is chromatographically isolated. Formation of the corresponding acid chloride (VIII) is finally performed by treatment of (VII) with (COCl)2 in refluxing benzene. Condensation between alcohol (V) and acid chloride (VIII) by means of DMAP in CH2Cl2 provides compound (IX), which is finally converted into the target product by removal of the allyl protecting groups by means of Pd(Ph3P)4 and morpholine.

1 Chiyo, J.; Ikeshiro, Y.; Cosentino, L.M.; Kashiwada, Y.; Fowke, K.; Lee, K.H.; Okabe, H.; Nagao, T.; 3,28-Di-O-(dimethylsuccinyl)-betulin isomers as anti-HIV agents. Bioorg Med Chem Lett 2001, 11, 2, 183.
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) 50064 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-1H-cyclopenta[a]chrysen-9-ol C30H50O2 详情 详情
(II) 46622 2,2-dimethylsuccinic acid C6H10O4 详情 详情
(III) 50065 4-[[(1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-3-yl]methoxy]-3,3-dimethyl-4-oxobutyric acid C36H58O5 详情 详情
(IV) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(V) 50066 1-[[(1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-3-yl]methyl] 4-allyl 2,2-dimethylsuccinate C39H62O5 详情 详情
(VI) 12234 2-Propen-1-ol; Allyl alcohol 107-18-6 C3H6O 详情 详情
(VII) 50067 4-(allyloxy)-3,3-dimethyl-4-oxobutyric acid C9H14O4 详情 详情
(VIII) 50068 allyl 4-chloro-2,2-dimethyl-4-oxobutanoate C9H13ClO3 详情 详情
(IX) 50069 4-[(1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-([[4-(allyloxy)-2,2-dimethyl-4-oxobutanoyl]oxy]methyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysen-9-yl] 1-allyl 2,2-dimethylsuccinate C48H74O8 详情 详情
Extended Information