Parallel synthesis of multi-branched oligosaccharides related to elicitor active pentasaccharide in rice cell based on orthogonal deprotection and glycosylation strategy

被引：32

作者：

Tanaka, H ^{[1
]}

Amaya, T ^{[1
]}

Takahashi, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Grad Sch Sci & Engn, Dept Appl Chem, Tokyo 1528552, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 15期

关键词：

combinatorial chemistry; branched oligosaccharides; phytoalexin elicitor; orthogonal deprotection; automated synthesizer;

D O I：

10.1016/S0040-4039(03)00553-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a parallel and efficient synthesis of multi-branched oligosaccharides 3a-g based upon the structure of the phytoalexin elicitor active branched pentasaccharide 2. One-pot sequential orthogonal deprotection of tetrasaccharide 5 with three different protecting groups provided each of seven glycosyl acceptors 4a-g. Glycosylation of the acceptors 4a-g, followed by deprotection provided branched oligosaccharides 3a-g. All the reaction processes from scaffold 5 to 3a-g except for final hydrogenolysis were achieved utilizing an automated synthesizer in a parallel fashion. (C) 2003 Published by Elsevier Science Ltd.

引用

页码：3053 / 3057

页数：5

共 32 条

[1] An easy and efficient approach for the installation of alkoxycarbonyl protecting groups on carbohydrate hydroxyls [J].