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【结 构 式】 
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【分子编号】16467 【品名】(2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-hydroxy-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 【CA登记号】 |
【 分 子 式 】C31H52N2O3 【 分 子 量 】500.76556 【元素组成】C 74.35% H 10.47% N 5.59% O 9.58% |
合成路线1
该中间体在本合成路线中的序号：(III)The acetylation of (2beta,3alpha,5alpha,16beta)-3-hydroxy-2,16-bis(piperidin-1-yl)androstan-17-one (I) with acetyl chloride in dichloromethane gives the corresponding 3-acetoxy derivative (II), which is reduced with NaBH4 in methanol - THF yielding (2beta,3alpha,5alpha,16,beta,17beta)-3-acetoxy-17-hydroxy-2,6-bis (piperidin-1-yl)androstane (III). The acylation of (III) with propionyl chloride in dichloromethane as before affords the 3-acetoxy-17-propionyloxy derivative (IV), which is finally quaternized with allyl bromide in dichloromethane.
| 【1】 Sleigh, T.; Carlyle, I.C.; Muir, A.W. (Akzo Nobel N.V.); Monoquaternary 2,16-bispiperidinylandrostane derivs. EP 0571012; JP 1995267984; US 5418226 . |
| 【2】 Graul, A.; Prous, J.; Castañer, J.; Org-9487. Drugs Fut 1994, 19, 10, 916. |
| 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) | 16465 | (2S,3S,5S,8R,9S,10S,13S,14S,16S)-3-hydroxy-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-17H-cyclopenta[a]phenanthren-17-one | C29H48N2O2 | 详情 | 详情 | |
| (II) | 16466 | (2S,3S,5S,8R,9S,10S,13S,14S,16S)-10,13-dimethyl-17-oxo-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C31H50N2O3 | 详情 | 详情 | |
| (III) | 16467 | (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-17-hydroxy-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate | C31H52N2O3 | 详情 | 详情 | |
| (IV) | 16468 | (2S,3S,5S,8R,9S,10S,13S,14S,16S,17R)-3-(acetoxy)-10,13-dimethyl-2,16-di(1-piperidinyl)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl propionate | C34H56N2O4 | 详情 | 详情 |