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【结 构 式】 
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【分子编号】56618 【品名】 【CA登记号】 |
【 分 子 式 】C26H33NO4 【 分 子 量 】423.55236 【元素组成】C 73.73% H 7.85% N 3.31% O 15.11% |
合成路线1
该中间体在本合成路线中的序号：(XXIX)Condensation of 3-methoxyandrosta-3,5,9(11)-trien-17-one (XI) with 3-hydroxypropionitrile (XXV) by means of LDA in THF provides 17a-(1-cyano-2- hydroxyethyl)-17b-hydroxyandrosta-4,9(11)-dien-3-one (XXVI), which is selectively monoacetylated by means of Ac2O in pyridine to yield monoacetate (XXVII). Dehydration of (XXVII) by means of SOCl2 in pyridine gives 20-cyano-21-acetoxypregna-4,9(11),17(20)-trien-3-one (XXVIII), which is treated with ethylene glycol, trimethyl orthoformate and TsOH in dichloromethane to afford the ethylene ketal (XXIX). Finally, compound (XXIX) is oxidized with KMnO4 in acetone/ethylene glycol and treated with NaHSO3 and HCOOH.
| 【1】 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; Bayes, M.; Anecortave Acetate. Drugs Fut 2002, 27, 11, 1039. |
| 【2】 Walker, J.A. (Pharmacia Corp.); Corticosteroids from 17-keto steroids via 20-cyano-DELTA17(20)-pregnanes. US 4600538 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 11295 | Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol | 107-21-1 | C2H6O2 | 详情 | 详情 | |
| (XI) | 18040 | (8S,10R,13S,14S)-3-methoxy-10,13-dimethyl-1,2,7,8,10,12,13,14,15,16-decahydro-17H-cyclopenta[a]phenanthren-17-one | C20H26O2 | 详情 | 详情 | |
| (XXV) | 14029 | Ethylene cyanohydrin; ECN; 3-Hydroxypropanenitrile | 109-78-4 | C3H5NO | 详情 | 详情 |
| (XXVI) | 56615 | 3-hydroxy-2-[(8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]propanenitrile | C22H29NO3 | 详情 | 详情 | |
| (XXVII) | 56616 | 2-cyano-2-[(8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl acetate | C24H31NO4 | 详情 | 详情 | |
| (XXVIII) | 56617 | 2-cyano-2-[(8S,10R,13S,14S)-10,13-dimethyl-3-oxo-1,2,3,6,7,8,10,12,13,14,15,16-dodecahydro-17H-cyclopenta[a]phenanthren-17-ylidene]ethyl acetate | C24H29NO3 | 详情 | 详情 | |
| (XXIX) | 56618 | C26H33NO4 | 详情 | 详情 |