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【结 构 式】

【分子编号】51630

【品名】(1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid

【CA登记号】

【 分 子 式 】C30H48O3

【 分 子 量 】456.70932

【元素组成】C 78.9% H 10.59% O 10.51%

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:(I)

Betulinic acid (I) was extracted from the dried leaves of Syzygium claviforum. Acylation of (I) with 2,2-dimethylsuccinic anhydride (II) in the presence of DMAP in refluxing pyridine furnished the target 3’,3’-dimethylsuccinyl betulinic acid along with minor amounts of the undesired 2’,2’-dimethyl regioisomer (III), which were separated by means of preparative HPLC.

3 Kashiwada, Y.; Wang, H.K.; Nagao, T.; Kitanaka, S.; Yasuda, I.; Fujioka, T.; Yamagishi, T.; Cosentino, L.M.; Kozuka, M.; Okabe, H.; Ikeshiro, Y.; Hu, C.Q.; Yeh, E.; Lee, K.H.; Anti-AIDS agents.30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. J Nat Prod 1998, 61, 9, 1090.
1 Kashiwada, Y.; et al.; Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J Med Chem 1996, 39, 5, 1016.
2 Hashimoto, F.; et al.; Anti-AIDS agents - XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. Bioorg Med Chem 1997, 5, 12, 2133.
4 Lee, K.-H.; Kashiwada, Y.; Hashimoto, F.; Cosentino, L.M.; Manak, M. (Biotech Research Laboratories; University of North Carolina); Betulinic acid derivs. and uses thereof. US 5679828; WO 9639033 .
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) 51630 (1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid C30H48O3 详情 详情
(II) 29295 3,3-dimethyldihydro-2,5-furandione 17347-61-4 C6H8O3 详情 详情
(III) 51631 (1R,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[(3-carboxy-2,2-dimethylpropanoyl)oxy]-1-isopropenyl-5a,5b,8,8,11a-pentamethylicosahydro-3aH-cyclopenta[a]chrysene-3a-carboxylic acid C36H56O6 详情 详情
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