(3aR,7aS)-1-[(1R)-5-ethyl-4,4-difluoro-1-methyl-5-[(trimethylsilyl)oxy]heptyl]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one -Drug Synthesis Database

【结构式】

【分子编号】44919

【品名】(3aR,7aS)-1-[(1R)-5-ethyl-4,4-difluoro-1-methyl-5-[(trimethylsilyl)oxy]heptyl]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one

【CA登记号】

【分子式】C₂₃H₄₀F₂O₂Si

【分子量】414.6517064

【元素组成】C 66.62% H 9.72% F 9.16% O 7.72% Si 6.77%

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：(XIII)

Protection of (XII) as the silyl ether (XIII), followed by Wittig reaction with the ylide resulting from the racemic phosphine oxide (XIV) furnished diene (XV) as a diastereomeric mixture. After desilylation with tetrabutylammonium fluoride, separation of the diastereoisomers by semipreparative RP-HPLC provided the title compound.

参考文献中间体

合成目标

【1】 Posner, G.H.; et al.; Noncalcemic, antiproliferative, transcriptionally active, 24-fluorinated hybrid analogues of the hormone 1alpha,25-dihydroxyvitamin D3. Synthesis and preliminary biological evaluation. J Med Chem 1998, 41, 16, 3008.
【2】 Wang, Q.; Lee, J.K.; Posner, G.H. (Johns Hopkins University); Non-calcemic, antiproliferative, transcriptionally active 24-fluorinated hybrid analogs of 1alpha,25-dihydroxyvitamin D3. US 6043386 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XII)	44918	(3aR,7aS)-1-[(1R)-5-ethyl-4,4-difluoro-5-hydroxy-1-methylheptyl]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one	C₂₀H₃₂F₂O₂	详情	详情
(XIII)	44919	(3aR,7aS)-1-[(1R)-5-ethyl-4,4-difluoro-1-methyl-5-[(trimethylsilyl)oxy]heptyl]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-4-one	C₂₃H₄₀F₂O₂Si	详情	详情
(XIV)	44920	2-[(3R,5R)-5-[[tert-butyl(dimethyl)silyl]oxy]-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-methylenecyclohexylidene]ethyl(diphenyl)phosphine oxide; [2-[(3R,5R)-5-[[tert-butyl(dimethyl)silyl]oxy]-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-methylenecyclohexylidene]ethyl](oxo)diphenylphosphorane	C₃₄H₅₃O₃PSi₂	详情	详情
(XV)	44921	[[3-[(Z)-2-((3aS,7aS)-1-[(1R)-5-ethyl-4,4-difluoro-1-methyl-5-[(trimethylsilyl)oxy]heptyl]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-4-ylidene)ethylidene]-5-([[tert-butyl(dimethyl)silyl]oxy]methyl)-4-methylenecyclohexyl]oxy](tert-butyl)dimethylsilane; (5R)-5-((3aS,7aS)-4-[(E)-2-[5-[[tert-butyl(dimethyl)silyl]oxy]-3-([[tert-butyl(dimethyl)silyl]oxy]methyl)-2-methylenecyclohexylidene]ethylidene]-7a-methyl-3,3a,5,6,7,7a-hexahydro-4H-inden-1-yl)-1,1-diethyl-2,2-difluorohexyl trimethylsilyl ether	C₄₅H₈₂F₂O₃Si₃	详情	详情

Extended Information