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【结 构 式】 
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【药物名称】 【化学名称】6beta-Amino-5alpha-cholestan-3beta-ol 【CA登记号】 【 分 子 式 】C27H49NO 【 分 子 量 】403.69768 |
【开发单位】Université de La Rochelle (Originator) 【药理作用】Antifungal Agents, ANTIINFECTIVE THERAPY |
合成路线1
Nitration of cholesteryl acetate (I) with nitric acid in acetic acid gave the 6-nitro derivative (II). Reduction of the D5 double bond of (II) with ethanolic NaBH4 at room temperature provided the 6-beta-nitro compound (III). Finally, reduction of the nitro group of (III) with concomitant deacetylation using LiAlH4 in refluxing Et2O yielded the title compound.
| 【1】 Beuchet, P.; el Kihel, L.; Dherbomez, M.; Charles, G.; Letourneux, Y.; Synthesis of 6(alpha,beta)-aminocholestanols as ergosterol biosynthesis inhibitors. Bioorg Med Chem Lett 1998, 8, 24, 3627. |
| 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) | 16813 | (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | 604-35-3 | C29H48O2 | 详情 | 详情 |
| (II) | 29597 | (3S,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-6-nitro-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C29H47NO4 | 详情 | 详情 | |
| (III) | 29599 | (3S,5S,6R,8S,9S,10R,13R,14S,17R)-17-[(1R)-1,5-dimethylhexyl]-10,13-dimethyl-6-nitrohexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C29H49NO4 | 详情 | 详情 |
Extended Information