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【结 构 式】 
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【分子编号】39210 【品名】(2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one 【CA登记号】 |
【 分 子 式 】C25H40O5 【 分 子 量 】420.5896 【元素组成】C 71.39% H 9.59% O 19.02% |
合成路线1
该中间体在本合成路线中的序号：(II)The ketalization of 2beta-ethoxy-3alpha-hydroxy-5alpha-pregnane-11,20-dione (I) with ethylene glycol (A) by means of p-toluenesulfonic acid in refluxing benzene gives the corresponding 20,20-ethylenedioxy derivative (II), which is treated with hydroxylamine hydrochloride and NaOH refluxing ethanol to yield 20,20-ethylenedioxy-2beta-ethoxy-3alpha-hydroxy-5alpha-pregnan-11-one 11-oxime (III). The reduction of (III) with Na in refluxing propanol (B) affords 11alpha-amino-20,20-ethylenedioxy-2beta-ethoxy-3alpha-hydroxy-5alpha-pregnan (IV), which is finally methylated with methyl iodide and K2CO3 or with formaldehyde and formic acid, and hydrolyzed with HCl or H2SO4.
| 【1】 Philips, G.H.; Ewan, G.; DE 2715078 . |
| 【2】 Hillier, K.; Castaner, J.; Blancafort, P.; Serradell, M.N.; Minaxolone. Drugs Fut 1980, 5, 12, 614. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (AI) | 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 |
| (B) | 29338 | 1-propanol | 71-23-8 | C3H8O | 详情 | 详情 |
| (I) | 39209 | (2S,3S,5S,8S,9S,10S,13S,14S,17S)-17-acetyl-2-ethoxy-3-hydroxy-10,13-dimethylhexadecahydro-11H-cyclopenta[a]phenanthren-11-one | C23H36O4 | 详情 | 详情 | |
| (II) | 39210 | (2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one | C25H40O5 | 详情 | 详情 | |
| (III) | 39211 | (2S,3S,5S,8S,9S,10S,13S,14S,17S)-2-ethoxy-3-hydroxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-11H-cyclopenta[a]phenanthren-11-one oxime | C25H41NO5 | 详情 | 详情 | |
| (IV) | 39212 | (2S,3S,5S,8S,9S,10S,11R,13S,14S,17S)-11-amino-2-ethoxy-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-ol | C25H43NO4 | 详情 | 详情 |