methyl 2-[2-((2S,3aR,4R,5S,6aR)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S)-3-[(1R,3S)-1-hydroxy-3-methylheptyl]oxiranyl]octahydro-2-pentalenyl)ethoxy]acetate -Drug Synthesis Database

【结构式】

【分子编号】14842

【品名】methyl 2-[2-((2S,3aR,4R,5S,6aR)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S)-3-[(1R,3S)-1-hydroxy-3-methylheptyl]oxiranyl]octahydro-2-pentalenyl)ethoxy]acetate

【CA登记号】

【分子式】C₂₉H₅₄O₆Si

【分子量】526.82966

【元素组成】C 66.12% H 10.33% O 18.22% Si 5.33%

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：(XXIVa)

This new mixture is submitted to a selective epoxidation with (-)-DIPT, titanium tetraisopropoxide and TBHP in order to obtain a mixture of the epoxy alcohol (XXIVa) and the unsaturated alcohol (XXIVb). A chromatographic separation of the mixture followed by desilylation with acetic acid in methanol gives the desired final product.

参考文献中间体

合成目标

【1】 Mealy, N.; Castaner, J.; Pimilprost. Drugs Fut 1996, 21, 4, 369.
【2】 Shimoju. T.; Tanno, N. (Sumitomo Pharmaceuticals Co., Ltd.); Manufacturing method of optically active carbacyclin derivs. JP 1991220158 .
【3】 Muraoka, M.; Nakamura, T.; Sugie, A.; Ono, K.; Yamamoto, M. (Sumitomo Pharmaceuticals Co., Ltd.); Bicyclooctane derivs. and their production and use. EP 0115954 .
【4】 Kawakami, H.; Muraoka, M.; Sugie, A.; Ono, K.; Kojima, A.; Syntheses of new 3-oxa-methano-PGI1 derivatives and their biological properties. Bioorg Med Chem Lett 1993, 3, 12, 2821-6.
【5】 Kawakami, H.; Kojima, A.; Shimoju, T.; Shimaji, K.; Nagata, H.; Muraoka, M.; Tanno, N.; Synthesis and structure-activity relationships of SM-10902, a novel drug for the treatment of peripheral circulatory insufficiency. 111th Annu Meet Pharmaceut Soc Jpn (March 28-30, Tokyo) 1991, Abst 29V 1-036.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXIIIa)	14840	methyl 2-(2-[(2S,3aR,4R,5S,6aR)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-[(E,3R,5S)-3-hydroxy-5-methyl-1-nonenyl]octahydro-2-pentalenyl]ethoxy)acetate	C₂₉H₅₄O₅Si	详情	详情
(XXIVb)	14841	methyl 2-(2-[(2R,3aS,4S,5R,6aS)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-[(E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]octahydro-2-pentalenyl]ethoxy)acetate	C₂₉H₅₄O₅Si	详情	详情
(XXIIIb)	14841	methyl 2-(2-[(2R,3aS,4S,5R,6aS)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-[(E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]octahydro-2-pentalenyl]ethoxy)acetate	C₂₉H₅₄O₅Si	详情	详情
(XXIVa)	14842	methyl 2-[2-((2S,3aR,4R,5S,6aR)-5-[[tert-butyl(dimethyl)silyl]oxy]-4-[(2S)-3-[(1R,3S)-1-hydroxy-3-methylheptyl]oxiranyl]octahydro-2-pentalenyl)ethoxy]acetate	C₂₉H₅₄O₆Si	详情	详情

Extended Information