Regio- and Stereocontrolled Synthesis of 2d-Deoxy Lewisx Pentasaccharide

被引：5
作者：
Zhang, Yanyan [1 ,2 ]
Dong, Dengxiang [1 ,2 ]
Qu, Huanhuan [1 ]
Sollogoub, Matthieu [1 ]
Zhang, Yongmin [1 ]
机构：
[1] Univ Paris 06, Inst Parisien Chim Mol, CNRS, UMR 7201, F-75005 Paris, France
[2] Guiyang Coll Tradit Chinese Med, Guiyang 550002, Peoples R China
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 35期
关键词：
Total synthesis; Carbohydrates; Glycosylation; Oligosaccharides; Regio-selectivity; Diastereoselectivity; CARBOHYDRATE-CARBOHYDRATE RECOGNITION; CELL-ADHESION; OLIGOSACCHARIDES; AGGREGATION; ANTIGENS; MODEL;
D O I：
10.1002/ejoc.201101062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of 2d-deoxy Lewisx pentasaccharide is described. Ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-a,beta-D-galactopyranoside was condensed with a diol of glucosamine to regio- and stereoselectively give the disaccharide, the C-2' position was then reduced after stereoselective fucosylation to afford a Lewisx trisaccharide analogue. Regioselective glycosylation of a known lactoside diol with this trisaccharide provided a pentasaccharide that, after deprotection, gave the target pentasaccharide.
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页码：7133 / 7139
页数：7
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