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【结 构 式】 
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【分子编号】56624 【品名】(8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-(1-phenoxyvinyl)-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one 【CA登记号】 |
【 分 子 式 】C27H32O3 【 分 子 量 】404.54928 【元素组成】C 80.16% H 7.97% O 11.86% |
合成路线1
该中间体在本合成路线中的序号：(XXXV)Reaction of 17a-ethynyl-9,11-didehydrotestosterone (IV) with phenylsulfinyl chloride and TEA in dichloromethane gives 21-(phenylsulfinyl)pregna-4,9(11),17(20),20-tetraen-3-one (VI), which is treated with phenol and NaOH in refluxing toluene to provide 20-(phenoxy)-21-(phenylsulfinyl)pregna-4,9(11),20-trien-3-one (XXXIV). The reaction of compound (XXXIV) with trimethyl phosphite and TEA in hot methanol affords 17a-hydroxy-20-(phenoxy)pregna-4,9(11),20-trien-3-one (XXXV), which is finally treated with Oxone and KOH in hot dichloromethane, and then acetylated with Ac2O, TEA and DMAP in THF/water.
| 【1】 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; Bayes, M.; Anecortave Acetate. Drugs Fut 2002, 27, 11, 1039. |
| 【2】 Sacks, C.E. (Pharmacia Corp.); Process and intermediates for the preparation of 17alpha-hydroxyprogesterones and corticoids from an enol steroid. EP 0186948 . |
| 【3】 Shephard, K.P.; Van Rheenen, V.H. (Pharmacia Corp.); Process for the preparation of steroids. CH 630394 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (IV) | 56596 | (8S,10R,13S,14S,17R)-17-ethynyl-17-hydroxy-10,13-dimethyl-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | C21H26O2 | 详情 | 详情 | |
| (VI) | 56598 | (8S,10R,13S,14S)-10,13-dimethyl-17-[2-(phenylsulfinyl)ethenylidene]-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | C27H30O2S | 详情 | 详情 | |
| (XXXIV) | 56623 | (8S,10R,13S,14S)-10,13-dimethyl-17-[(Z)-1-phenoxy-2-(phenylsulfinyl)ethylidene]-7,8,10,12,13,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3(2H,6H)-one | C33H36O3S | 详情 | 详情 | |
| (XXXV) | 56624 | (8S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-17-(1-phenoxyvinyl)-1,2,6,7,8,10,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one | C27H32O3 | 详情 | 详情 |