(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(2-oxoethyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl benzoate -Drug Synthesis Database

【结构式】

【分子编号】52847

【品名】(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(2-oxoethyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl benzoate

【CA登记号】

【分子式】C₂₀H₂₄O₆

【分子量】360.40696

【元素组成】C 66.65% H 6.71% O 26.64%

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：(XX)

The second epoxide function was introduced into (XVIII) upon treatment with m-chloroperbenzoic acid, yielding (XIX). Oxidation of the primary alcohol of (XIX) to aldehyde (XX) was effected by means of Dess-Martin periodinane reagent. Subsequent Wittig reaction of aldehyde (XX) with isopropylidene triphenylphosphorane furnished olefin (XXI). The chiral fumagillol (-)-(XXII) was then obtained by hydrolysis of the benzoate ester (XXI) in the presence of methanolic K2CO3. Finally, condensation of alcohol (-)-(XXII) with the acid chloride (XXIII) led to the title compound.

参考文献中间体

合成目标

【1】 Taber, D.F.; et al.; Synthesis of (-)-fumagillin. J Am Chem Soc 1999, 121, 23, 5589.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XVIII)	52845	(3R,4S,5S,6R)-4-[(E)-4-hydroxy-1-methyl-1-butenyl]-5-methoxy-1-oxaspiro[2.5]oct-6-yl benzoate	C₂₀H₂₆O₅	详情	详情
(XIX)	52846	(3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxyethyl)-2-methyloxiranyl]-5-methoxy-1-oxaspiro[2.5]oct-6-yl benzoate	C₂₀H₂₆O₆	详情	详情
(XX)	52847	(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(2-oxoethyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl benzoate	C₂₀H₂₄O₆	详情	详情
(XXI)	52848	(3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl benzoate	C₂₃H₃₀O₅	详情	详情
(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
(XXIII)	52849	(2E,4E,6E,8E)-2,4,6,8-decatetraenedioyl dichloride	C₁₀H₈Cl₂O₂	详情	详情

Extended Information