(8S,9S,13R,14S,17R)-17-(2-hydroxyethyl)-3-isopropoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-one -Drug Synthesis Database

【结构式】

【分子编号】53014

【品名】(8S,9S,13R,14S,17R)-17-(2-hydroxyethyl)-3-isopropoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-one

【CA登记号】n/a

【分子式】C₂₃H₃₂O₃

【分子量】356.50528

【元素组成】C 77.49% H 9.05% O 13.46%

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：(XVIII)

The intermediate diol (XV) was also obtained by an alternative procedure. Aromatization of enone (IV) in the presence of isopropanol, I2 and O2 gave rise to the isopropoxy ketone (XVIII). The free hydroxyl group was then protected as the tetrahydropyranyl ether (V). Alkylation at the alpha position of the keto group of (V) , followed by acidic hydrolysis of the tetrahydropyranyl group, furnished the alpha-methyl ketone (VI). The keto group of (VI) was subsequently reduced by hydrogenation over Pd/C to afford (XIX). Further isopropyl ether cleavage with AlCl3 afforded diol (XV).

参考文献中间体

合成目标

【1】 Peters, R.H.; Tanabe, M.; Chao, W.-R.; Johansson, J.G.; Ryan, K.J.; Liu, J. (SRI International); Synthesis of anti-estrogenic acid and other therapeutic steroids from 21-hydroxy-19-norpregna-4-en-3-one. WO 0158919 .

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)	53001	(8R,9S,13R,14S,17R)-17-(2-hydroxyethyl)-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one	n/a	C₂₀H₃₀O₂	详情	详情
(V)	53002	(8S,9S,13R,14S,17R)-3-isopropoxy-13-methyl-17-[2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-one	n/a	C₂₈H₄₀O₄	详情	详情
(VI)	53003	(7S,8S,9S,13R,14S,17R)-17-(2-hydroxyethyl)-3-isopropoxy-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-one	n/a	C₂₄H₃₄O₃	详情	详情
(XV)	53011	(7R,8S,9S,13R,14S,17R)-17-(2-hydroxyethyl)-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-ol	n/a	C₂₁H₃₀O₂	详情	详情
(XVIII)	53014	(8S,9S,13R,14S,17R)-17-(2-hydroxyethyl)-3-isopropoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-one	n/a	C₂₃H₃₂O₃	详情	详情
(XIX)	53015	2-[(7R,8S,9S,13R,14S,17R)-3-isopropoxy-7,13-dimethyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl]-1-ethanol	n/a	C₂₄H₃₆O₂	详情	详情

Extended Information