(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 -Drug Synthesis Database

【结构式】

【分子编号】56623

【品名】(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

【CA登记号】

【分子式】C₃₃H₃₆O₃S

【分子量】512.71304

【元素组成】C 77.31% H 7.08% O 9.36% S 6.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(XXXIV)

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.

参考文献中间体

合成目标

【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	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

Extended Information