(8R,9S,10R,13S,14S)-13-ethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione -Drug Synthesis Database

【结构式】

【分子编号】33950

【品名】(8R,9S,10R,13S,14S)-13-ethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione

【CA登记号】

【分子式】C₁₉H₂₆O₂

【分子量】286.41424

【元素组成】C 79.68% H 9.15% O 11.17%

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：(I)

18-Methyl-4-oestrene-3,17-dione (I) is hydroxylated by fermentation with Penicillium raistrickii giving the 15alpha-hydroxy compound (II), which is ketalized with 2,2-dimethylpropanediol (A), triethyl orthoformate and p-toluenesulfonic acid in CH2Cl2 giving a mixture of the DELTA(5-6) and DELTA(5-10)-ketals (IIIa-b). These ketals are mesylated witn methanesulfonyl chloride in pyridine yielding the mesyl ester (IVa-b), which is treated with sodium acetate in DMF to afford the oestradiene ketal (Va-b). Finally, this compound is treated with ethynylmagnesium bromide (B) and refluxed with oxalic acid (C) in methanol.

参考文献中间体

合成目标

【1】 Hofmeister, H.; Wiechert, R.; Annen, K.; Laurent, H.; Steinbeck, H.; Steroids and pharmaceutical compositions thereof. BE 0847090; FR 2326927; GB 1569135; JP 52046060; US 4081537 .
【2】 Castaner, J.; Blancafort, P.; Gestodene. Drugs Fut 1977, 2, 12, 805.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	12641	Neopentyl glycol; 2,2-Dimethyl-1,3-propanediol	126-30-7	C₅H₁₂O₂	详情	详情
(B)	17778	ETHYNYLMAGNESIUM BROMIDE; bromo(ethynyl)magnesium	4301-14-8	C₂HBrMg	详情	详情
(IIIa)	33952			C₂₄H₃₆O₄	详情	详情
(IIIb)	33953			C₂₄H₃₆O₄	详情	详情
(IVa)	33954			C₂₇H₄₂O₄S	详情	详情
(IVb)	33955			C₂₇H₄₂O₄S	详情	详情
(Va)	33956			C₂₄H₃₄O₃	详情	详情
(Vb)	33957			C₂₄H₃₄O₃	详情	详情
(I)	33950	(8R,9S,10R,13S,14S)-13-ethyl-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione		C₁₉H₂₆O₂	详情	详情
(II)	33951	(8R,9S,10R,13S,14S,15S)-13-ethyl-15-hydroxy-7,8,9,10,11,12,13,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17(2H,6H)-dione		C₁₉H₂₆O₃	详情	详情
(C)	15713	Oxalic acid	144-62-7	C₂H₂O₄	详情	详情

Extended Information