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【结 构 式】

【分子编号】20087

【品名】(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(3-pyridinyl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate

【CA登记号】

【 分 子 式 】C26H33NO2

【 分 子 量 】391.55356

【元素组成】C 79.76% H 8.49% N 3.58% O 8.17%

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:(V)

Treatment of dehydroepiandrosterone 3-acetate (I) with triflic anhydride and 2,6-di-tert-butyl-4-methylpyridine provided the desired enol triflate (III) along with some 3,5-diene (II), which were separated by column chromatography. Subsequent coupling of triflate (III) with pyridylborane (IV) using bis(triphenylphosphine)- palladium(II) chloride as the catalyst afforded the (3-pyridyl)androstadiene (V), which after hydrolysis of the acetate ester with NaOH provided the target compound.

1 Potter, G.A.; et al.; Novel steroidal inhibitors of human cytochrome P450(17alpha) (17alpha-hydroxylase-C17,20-lyase): Potential agents for the treatment of prostatic cancer. J Med Chem 1995, 38, 13, 2463.
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) 20083 Prasterone acetate;3b-Hydroxy-5-androstene-17-one acetate;Dehydroisoandrosterone acetate;Dehydroepiandrosterone 3-acetate;Dehydroepiandrosterone acetate;(3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate 853-23-6 C21H30O3 详情 详情
(II) 20084 (8R,9S,10R,13S,14S)-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate C20H25F3O3S 详情 详情
(III) 20085 (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-[[(trifluoromethyl)sulfonyl]oxy]-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C22H29F3O5S 详情 详情
(IV) 20086 3-(diethylboryl)pyridine C9H14BN 详情 详情
(V) 20087 (3S,8R,9S,10R,13S,14S)-10,13-dimethyl-17-(3-pyridinyl)-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate C26H33NO2 详情 详情
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