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

【结构式】

【分子编号】59422

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

【CA登记号】

【分子式】C₂₀H₂₆O₂

【分子量】298.42524

【元素组成】C 80.5% H 8.78% O 10.72%

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：(XIX)

Friedel-Crafts acylation of 3-deoxyestradiol acetate (XIX) employing acetyl chloride and AlCl3 afforded the 2-acetylated compound (XX) as the major isomer. This was subjected to Baeyer-Villiger oxidation with peracetic acid to give diacetate (XXI), which was further hydrolyzed to diol (XXII) under basic conditions. Alkylation of the phenolic hydroxyl using dimethyl sulfate in the presence of KOH furnished the methyl ether (XXIII). After esterifying the aliphatic alcohol with acetic anhydride in pyridine, the resultant compound (XXIV) was subjected to a new cycle of Friedel-Crafts acetylation and Baeyer-Villiger oxidation yielding the 3,17-diacetate (XXVI). Finally, basic hydrolysis of the acetate esters provided the target compound.

参考文献中间体

合成目标

【1】 Nambara, T.; et al.; Studies on steroid conjugates. III. New syntheses of 2-methoxyestrogens. Chem Pharm Bull 1970, 18, 3, 474.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XIX)	59422	(8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₀H₂₆O₂	详情	详情
(XX)	59423	(8R,9S,13S,14S,17S)-2-acetyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₂H₂₈O₃	详情	详情
(XXI)	59424	(8R,9S,13S,14S,17S)-17-(acetyloxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yl acetate	C₂₂H₂₈O₄	详情	详情
(XXII)	59425	(8R,9S,13S,14S,17S)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-2,17-diol	C₁₈H₂₄O₂	详情	详情
(XXIII)	59426	(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol	C₁₉H₂₆O₂	详情	详情
(XXIV)	59427	(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₁H₂₈O₃	详情	详情
(XXV)	59428	(8R,9S,13S,14S,17S)-3-acetyl-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl acetate	C₂₃H₃₀O₄	详情	详情
(XXVI)	59429	(8R,9S,13S,14S,17S)-17-(acetyloxy)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl acetate	C₂₃H₃₀O₅	详情	详情

Extended Information