{(1R,2S,3S,4R)-2-[(1E)-1,5-dimethyl-1,4-hexadienyl]-1,3,4-trihydroxycyclohexyl}methyl methanesulfonate -Drug Synthesis Database

【结构式】

【分子编号】52862

【品名】{(1R,2S,3S,4R)-2-[(1E)-1,5-dimethyl-1,4-hexadienyl]-1,3,4-trihydroxycyclohexyl}methyl methanesulfonate

【CA登记号】

【分子式】C₁₆H₂₈O₆S

【分子量】348.46072

【元素组成】C 55.15% H 8.1% O 27.55% S 9.2%

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：(XXXV)

The primary alcohol group of (XXXIV) was selectively converted to mesylate (XXXV), which was subsequently treated with methanolic NaOH to afford the spiro-epoxide (XXXVI). Sharpless epoxidation of diene (XXXVI) in the presence of tert-butyl hydroperoxide and vanadyl acetylacetonate gave rise to the bis-epoxide (XXXVII) as the major diastereoisomer. Finally, regioselective hydroxyl group alkylation in (XXXVII) under Williamson's synthesis conditions furnished the racemic fumagillol (+/-)-(XXII).

参考文献中间体

合成目标

【1】 Vosburg, D.A.; et al.; A concise synthesis of fumagillol. Angew Chem. Int Ed 1999, 38, 7, 971.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXII)	13712	(3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-ol	C₁₆H₂₆O₄	详情	详情
(XXXIV)	52861	(1R,2S,3S,4R)-3-[(1E)-1,5-dimethyl-1,4-hexadienyl]-4-(hydroxymethyl)-1,2,4-cyclohexanetriol	C₁₅H₂₆O₄	详情	详情
(XXXV)	52862	{(1R,2S,3S,4R)-2-[(1E)-1,5-dimethyl-1,4-hexadienyl]-1,3,4-trihydroxycyclohexyl}methyl methanesulfonate	C₁₆H₂₈O₆S	详情	详情
(XXXVI)	52863	(3R,4S,5S,6R)-4-[(1E)-1,5-dimethyl-1,4-hexadienyl]-1-oxaspiro[2.5]octane-5,6-diol	C₁₅H₂₄O₃	详情	详情
(XXXVII)	52864	(3R,4S,5S,6R)-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octane-5,6-diol	C₁₅H₂₄O₄	详情	详情

Extended Information