(7aR)-1-((1R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-1,5-dimethyl-5-nitrohexyl)-7a-methyloctahydro-4H-inden-4-one -Drug Synthesis Database

【结构式】

【分子编号】21830

【品名】(7aR)-1-((1R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-1,5-dimethyl-5-nitrohexyl)-7a-methyloctahydro-4H-inden-4-one

【CA登记号】

【分子式】C₂₄H₄₅NO₄Si

【分子量】439.71114

【元素组成】C 65.56% H 10.32% N 3.19% O 14.55% Si 6.39%

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：(VI)

Condensation of aldehyde (I) with 2-nitropropane (II) using tert-butyldimethylsilyl chloride, tetrabutylammonium fluoride and triethylamine afforded a mixture of diastereomeric nitroaldol products (III). After separation by column chromatography, the desired isomer was protected as the tert-butyldimethylsilyl ether (IV). Deprotection of the benzoate ester of (IV) was carried out by reduction with diisobutylaluminum hydride to provide alcohol (V), which was then oxidized to the corresponding ketone (VI) with pyridinium chlorochromate. Wittig reaction of (VI) with phosphorane (VII) provided the bromomethylene compound (VIII).

参考文献中间体

合成目标

【1】 Oshida, J.; et al.; Synthesis and biological evaluation of 1alpha,24-dihydroxy-25-nitrovitamin D3. Bioorg Med Chem Lett 1999, 9, 3, 381.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	21818	(4S,7aR)-7a-methyl-1-[(1R)-1-methyl-4-oxobutyl]octahydro-1H-inden-4-yl benzoate		C₂₂H₃₀O₃	详情	详情
(II)	21819	2-nitropropane	79-46-9	C₃H₇NO₂	详情	详情
(III)	21820	(4S,7aR)-1-[(1R)-4-hydroxy-1,5-dimethyl-5-nitrohexyl]-7a-methyloctahydro-1H-inden-4-yl benzoate		C₂₅H₃₇NO₅	详情	详情
(IV)	21828	(4S,7aR)-1-((1R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-1,5-dimethyl-5-nitrohexyl)-7a-methyloctahydro-1H-inden-4-yl benzoate		C₃₁H₅₁NO₅Si	详情	详情
(V)	21829	(4S,7aR)-1-((1R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-1,5-dimethyl-5-nitrohexyl)-7a-methyloctahydro-1H-inden-4-ol		C₂₄H₄₇NO₄Si	详情	详情
(VI)	21830	(7aR)-1-((1R,4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-1,5-dimethyl-5-nitrohexyl)-7a-methyloctahydro-4H-inden-4-one		C₂₄H₄₅NO₄Si	详情	详情
(VII)	21831	(bromomethyl)(triphenyl)phosphonium bromide	1034-49-7	C₁₉H₁₇Br₂P	详情	详情
(VIII)	21832	(1S,4R)-4-[(7aR)-4-[(E)-bromomethylidene]-7a-methyloctahydro-1H-inden-1-yl]-1-(1-methyl-1-nitroethyl)pentyl tert-butyl(dimethyl)silyl ether; [[(1S,4R)-4-[(7aR)-4-[(E)-bromomethylidene]-7a-methyloctahydro-1H-inden-1-yl]-1-(1-methyl-1-nitroethyl)pentyl]oxy](tert-butyl)dimethylsilane		C₂₅H₄₆BrNO₃Si	详情	详情

Extended Information