(1S,3aR,4S,5S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-diol -Drug Synthesis Database

【结构式】

【分子编号】45536

【品名】(1S,3aR,4S,5S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-diol

【CA登记号】

【分子式】C₁₀H₁₇BrO₂

【分子量】249.14778

【元素组成】C 48.21% H 6.88% Br 32.07% O 12.84%

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)

The bromination of the Hajos dione (XI) with t-Bu-Cu, DIBAL and Br2 in HMPA/THF gives the bromo derivative (XII), which is reduced with LiAlH(t-BuO)3 in THF to yield the diol (XIII). The dehydrobromination of (XIII) with KH in HMPA affords the epoxide (XIV), which is oxidized with pyridinium dichromate (PDC) in dichloromethane to provide the ketoepoxide (XV). The Wittig condensation of (XV) with phosphonium salt (XVI) by means of potassium tert-butoxide gives the ethylidene epoxide (XVII), which is finally opened with LiAlH4 in THF to yield the target intermediate (I).

参考文献中间体

合成目标

【1】 Liu, W.; Daniewski, A.R.; A novel silycopper catalyst for the reductivo bromination of hajos dione. Improved preparation of a CD synthon for teh synthesis of vitamin D. J Org Chem 2001, 66, 2, 626.

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)	42566	(3aR,4S,7aS)-1-[(Z)ethylidene]-7a-methyloctahydro-1H-inden-4-ol		C₁₂H₂₀O	详情	详情
(XI)	45534	(7aS)-7a-methyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione	17553-86-5	C₁₀H₁₂O₂	详情	详情
(XII)	45535	(3aR,4S,7aS)-4-bromo-7a-methylhexahydro-1H-indene-1,5(4H)-dione	2706-38-9	C₁₀H₁₃BrO₂	详情	详情
(XIII)	45536	(1S,3aR,4S,5S,7aS)-4-bromo-7a-methyloctahydro-1H-indene-1,5-diol		C₁₀H₁₇BrO₂	详情	详情
(XIV)	45537	(1aS,3aS,4S,6aR,6bR)-3a-methyloctahydro-1aH-indeno[4,5-b]oxiren-4-ol		C₁₀H₁₆O₂	详情	详情
(XV)	45538	(1aS,3aS,6aR,6bR)-3a-methyloctahydro-4H-indeno[4,5-b]oxiren-4-one		C₁₀H₁₄O₂	详情	详情
(XVI)	11717	Ethyl(triphenyl)phosphonium bromide; (Ethyl)triphenylphosphonium bromide	1530-32-1	C₂₀H₂₀BrP	详情	详情
(XVII)	45539	(1aS,3aS,6aR,6bR)-4-[(Z)ethylidene]-3a-methyloctahydro-4H-indeno[4,5-b]oxirene		C₁₂H₁₈O	详情	详情

Extended Information