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【结 构 式】

【分子编号】56627

【品名】2-[(8S,10R,13S,14S)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate

【CA登记号】23460-76-6

【 分 子 式 】C23H28O4

【 分 子 量 】368.47292

【元素组成】C 74.97% H 7.66% O 17.37%

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:(XXXVIII)

Condensation of 3-methoxyandrosta-3,5,9(11)-trien-17-one (XI) with 2-chlorovinyl ethyl ether (XXXVI) by means of BuLi in THF gives 20-chloro-3-oxopregna-4,9(11),17(20)-trien-21-al (XXXVII), which is treated with Ac2O and AcOK in hot DMF to yield 21-(acetoxy)pregna-4,9(11),16-triene-3,20-dione (XXXVIII), Reaction of compound (XXXVIII) with RhCl(PPh3)3 and triethylsilane in hot dichloromethane affords 21-(acetoxy)-20-(triethyl-silyloxy)pregna-4,9(11),17(20)-trien-3-one (XXXIX), which is finally oxidized with peracetic acid in toluene, quenched with SO2 and treated with TEA.

1 Castaner, J.; Sorbera, L.A.; Leeson, P.A.; Bayes, M.; Anecortave Acetate. Drugs Fut 2002, 27, 11, 1039.
2 Van Rheenen, V.H.; Hessler, E.J. (Pharmacia Corp.); Synthesis of 16-unsaturated pregnanes from 17-keto steroids. US 4216159 .
3 Walker, J.A. (Pharmacia Corp.); DELTA16-20-keto steroid conversion to 17alpha-hydroxy-20-keto steroids. US 4568492 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(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
(XXXVI) 56625 (E)-1-chloro-2-ethoxyethene; (E)-2-chloroethenyl ethyl ether C4H7ClO 详情 详情
(XXXVII) 56626 2-chloro-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]acetaldehyde C21H25ClO2 详情 详情
(XXXVIII) 56627 2-[(8S,10R,13S,14S)-10,13-dimethyl-3-oxo-2,3,6,7,8,10,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl acetate 23460-76-6 C23H28O4 详情 详情
(XXXIX) 56628 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]-2-[(triethylsilyl)oxy]ethyl acetate C29H44O4Si 详情 详情
Extended Information