Synthesis of a C-glycoside analogue of β-D-galactosylthreonine

被引：29

作者：

Gustafsson, T ^{[1
]}

Saxin, M ^{[1
]}

Kihlberg, J ^{[1
]}

机构：

[1] Umea Univ, Dept Chem, SE-90187 Umea, Sweden

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 06期

关键词：

D O I：

10.1021/jo026758d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A C-linked analogue of beta-D-galactosylthreonine has been prepared from 2,3,4,6-tetra-O-benzyl-D-galactopyranolactone (1) in 14 steps. Three stereogenic centers were created during the synthesis, with the anomeric center of the C-glycoside being generated first by addition of a Grignard reagent to 1 and subsequent reduction of the intermediate hemiacetal with triethylsilane. The two stereogenic centers in the threonine moiety were both established by alkylation of Evans' chiral N-acyloxazolidinone enolates.

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页码：2506 / 2509

页数：4

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