ortho-Methylphenylthioglycosides as glycosyl building blocks for preactivation-based oligosaccharide synthesis

被引：18
作者：
Peng, Peng [1 ]
Xiong, De-Cai [1 ]
Ye, Xin-Shan [1 ]
机构：
[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
来源：
CARBOHYDRATE RESEARCH | 2014年 / 384卷
基金：
中国国家自然科学基金;
关键词：
o-Methylphenylthioglycoside; Preactivation; Oligosaccharide; Aglycon transfer; Glycosylation; INTERMOLECULAR AGLYCON TRANSFER; CHEMOSELECTIVE GLYCOSYLATIONS; THIOGLYCOSIDES; DERIVATIVES; PENTASACCHARIDE; STRATEGY;
D O I：
10.1016/j.carres.2013.11.009
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：
Thioglycosides are widely used in orthogonal glycosylation, armed-disarmed chemoselective glycosylation, and preactivation-based glycosylation. Nevertheless, aglycon transfer occasionally occurred in the glycosylation process of thioglycosides. This problem was also encountered in preactivation-based reactions, which limited the applications of preactivation-based glycosylation to some extent. To tackle this problem, sterically hindered aglycon ortho-methylphenylthioglycosides were introduced as glycosyl building blocks. These thioglycosides prevented the aglycon transfer and enhanced the efficiency of glycosyl coupling reactions, especially in the reactions of disarmed donors with armed acceptors. Moreover, these thioglycosides were employed in preactivation-based one-pot oligosaccharide assembly. (C) 2013 Elsevier Ltd. All rights reserved.
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页码：1 / 8
页数：8
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