[3-(2,2-Dimethoxyethyl)-2-oxiranyl]methanol -Drug Synthesis Database

【结构式】

【分子编号】12228

【品名】[3-(2,2-Dimethoxyethyl)-2-oxiranyl]methanol

【CA登记号】

【分子式】C₇H₁₄O₄

【分子量】162.18576

【元素组成】C 51.84% H 8.7% O 39.46%

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：(XXXIII)

Finally, the first total synthesis of stavudine has also been described: Starting from epoxide (XXXIII), readily available in four steps from crotonaldehyde, compound (XXXIV) is obtained after reaction with selenophenol and diethylaluminum fluoride in dichloromethane. Reaction of (XXXIV) with hydrochloric acid in methanol-dichloromethane gives (XXXV), which is acetylated to give (XXXVI). Introduction of silylated thymine (XXIII) catalyzed by tert-butyldimethylsilyl triflate in dichloromethane affords compound (XXXVII), which is converted to (XXXVIII) on treatment with m-chloroperbenzoic acid in dichloromethane. Deprotection of (XXXVIII) provides an anomeric mixture of stavudine and its alpha-anomer (XXXIX).

参考文献中间体

合成目标

【1】 Gardiner, J.M.; Jung, M.E.; Synthesis of antiviral nucleosides from crotonaldehyde. Part 3. Total synthesis of didehydrodideoxythymidine (d4T). Tetrahedron Lett 1992, 33, 27, 3841-4.
【2】 Robinson, C.; Castaner, J.; Stavudine. Drugs Fut 1994, 19, 10, 925.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXIII)	12218	5-Methyl-2,4-bis[(trimethylsilyl)methyl]pyrimidine	C₁₃H₂₆N₂Si₂	详情	详情
(XXXIII)	12228	[3-(2,2-Dimethoxyethyl)-2-oxiranyl]methanol	C₇H₁₄O₄	详情	详情
(XXXIV)	12229	(2R,3S)-5,5-Dimethoxy-3-(phenylselanyl)-1,2-pentanediol	C₁₃H₂₀O₄Se	详情	详情
(XXXV)	12230	[(2R,3S)-5-Methoxy-3-(phenylselanyl)tetrahydro-2-furanyl]methanol	C₁₂H₁₆O₃Se	详情	详情
(XXXVI)	12231	[(2R,3S)-5-methoxy-3-(phenylselanyl)tetrahydro-2-furanyl]methyl acetate	C₁₄H₁₈O₄Se	详情	详情
(XXXVII)	12185	2-Diazo-3-oxo-5-[4-oxo-3-(2-phenoxy-acetamido)-azetidin-2-yl]-pentanoic acid 4-nitro-benzyl ester	C₂₃H₂₁N₅O₈	详情	详情
(XXXVIII)	12233	[(2S)-5-[5-methyl-2,4-dioxo-3,4-dihydro-1(2H)-pyrimidinyl]-2,5-dihydro-2-furanyl]methyl acetate	C₁₂H₁₄N₂O₅	详情	详情

Extended Information