Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD

被引：20

作者：

Attolino, Emanuele ^{[1
]}

Cumpstey, Ian ^{[1
]}

Fairbanks, Antony J. ^{[1
]}

机构：

[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England

来源：

CARBOHYDRATE RESEARCH | 2006年 / 341卷 / 10期

基金：

英国工程与自然科学研究理事会;

关键词：

carbohydrates; intramolecular; glycosylation; allyl; intramolecular aglycon delivery; thioglycosides; glycoproteins;

D O I：

10.1016/j.carres.2006.02.022

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of the tetrasaccharide alpha-D-Glcp-(1 -> 2)-alpha-D-Glcp-(1 -> 3)-alpha-D-Glcp-(1 -> 3)-alpha-D-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：1609 / 1618

页数：10

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