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【结 构 式】 
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【药物名称】 【化学名称】3beta-(3-Carboxy-3-methylbutyryloxy)oleanan-28-oic acid 【CA登记号】 【 分 子 式 】C36H58O6 【 分 子 量 】586.86006 |
【开发单位】Biotech Research Laboratories (Originator), Chinese Academy of Sciences (Originator), University of North Carolina (Originator) 【药理作用】AIDS Medicines, Anti-HIV Agents, ANTIINFECTIVE THERAPY |
合成路线1
Dihydrooleanolic acid (VI) was prepared from oleanolic acid (I) as follows. Acylation of (I) with Ac2O in pyridine gave 3-acetoxy oleanolic acid (II), which was converted to the corresponding methyl ester (III) upon treatment with diazomethane. Subsequent epoxidation of (III) by means of m-chloroperbenzoic acid afforded the 12,13-epoxy derivative (IV). Rearrangement of epoxide (IV) by refluxing with boron trifluoride etherate in benzene led to ketone (V). Wolff-Kishner reduction of the keto group of (V) with hydrazine and KOH in tripolyethylene glycol furnished dihydrooleanolic acid (VI). The title compound was then obtained by esterification of (VI) with 2,2-dimethylsuccinic anhydride (VII).
| 【1】 Zhu, Y.-M.; Shen, J.-K.; Wang, H.-K.; Cosentino, L.M.; Lee, K.-H.; Synthesis and anti-HIV activity of oleanolic acid derivatives. Bioorg Med Chem Lett 2001, 11, 24, 3115. |
| 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) | 59920 | (6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picenecarboxylic acid | C30H48O3 | 详情 | 详情 | |
| (II) | 59921 | (6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picenecarboxylic acid | C32H50O4 | 详情 | 详情 | |
| (III) | 59922 | methyl (6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-4a(2H)-picenecarboxylate | C33H52O4 | 详情 | 详情 | |
| (IV) | 59923 | methyl (4aR,4bR,5aS,6aR,6bR,9S,10aR,12aR,12bS)-9-(acetyloxy)-3,3,6b,10,10,12a,12b-heptamethyloctadecahydro-1H-piceno[12b,13-b]oxirene-14a(5aH)-carboxylate | C33H52O5 | 详情 | 详情 | |
| (V) | 59924 | methyl (6aR,6bR,8aR,10S,12aR,12bR,14aR,14bS)-10-(acetyloxy)-2,2,6a,6b,9,9,12a-heptamethyl-14-oxoicosahydro-4a(2H)-picenecarboxylate | C33H52O5 | 详情 | 详情 | |
| (VI) | 59925 | (6aR,6bR,8aR,10S,12aR,12bR,14aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethylicosahydro-4a(2H)-picenecarboxylic acid | C30H50O3 | 详情 | 详情 | |
| (VII) | 29295 | 3,3-dimethyldihydro-2,5-furandione | 17347-61-4 | C6H8O3 | 详情 | 详情 |