一种合成3-C-烷基（或3-C-苯基）-2,3-二脱氧-D-赤藓糖-1,4-戊酮糖内酯的路线：2(3H)-呋喃酮合成中的中间体。

A synthetic route to 3-C-alkyl (or 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones: intermediates in the synthesis of 2(3H)-furanones.

作者信息

Raveendranath P C, Blazis V J, Agyei-Aye K, Hebbler A K, Gentile L N, Hawkins E S, Johnson S C, Baker D C

机构信息

Department of Chemistry, University of Tennessee, Knoxville 37996-1600.

出版信息

Carbohydr Res. 1994 Feb 3;253:207-23. doi: 10.1016/0008-6215(94)80066-9.

DOI:10.1016/0008-6215(94)80066-9

PMID:8156548

Abstract

A series of 3-C-alkyl- (and 3-C-phenyl-) 2,3-dideoxy-D-erythro-pentono-1,4-lactones, compounds which are important in the synthesis of modified nucleosides and antibiotic sugars, were synthesized from D-ribonolactone. By a route that proceeded via 5-O-protected D-ribonolactone, 5-O-protected 2,3-dideoxy-D-glycero-pent-2-enono-1,4-lactones were synthesized and reacted with R2CuLi or a complex PhSCu(RMgBr)n to give respectively the 3-C-alkyl or 3-C-phenyl compounds. Details of the preparation of the O-protected intermediates, as well as the selection of the organometallic reagents, are provided.

摘要

一系列3-C-烷基-（和3-C-苯基）-2,3-二脱氧-D-赤藓糖戊糖-1,4-内酯，这些化合物在修饰核苷和抗生素糖的合成中很重要，是由D-核糖内酯合成的。通过一条经由5-O-保护的D-核糖内酯的路线，合成了5-O-保护的2,3-二脱氧-D-甘油戊-2-烯糖-1,4-内酯，并使其与R2CuLi或配合物PhSCu(RMgBr)n反应，分别得到3-C-烷基或3-C-苯基化合物。文中提供了O-保护中间体的制备细节以及有机金属试剂的选择。