6-O-Amino-2-O-carboxymethyl Glucopyranoside as Novel Glycoaminoxy Acid Building Block for the Construction of Oligosaccharide Mimetics

被引：15

作者：

Song, Zhuo ^{[1
,2
]}

He, Xiao-Peng ^{[1
,2
,3
]}

Chen, Guo-Rong ^{[1
,2
]}

Xie, Juan ^{[3
]}

机构：

[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China

[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

[3] ENS Cachan, PPSM, CNRS, F-94230 Cachan, France

来源：

SYNTHESIS-STUTTGART | 2011年 / 17期

基金：

中国国家自然科学基金;

关键词：

aminoxy acids; glycoaminoxy acids; oligosaccharide mimetics; carbohydrates; oligomers; SUGAR AMINO-ACIDS; PEPTIDES; REAGENTS; ETHERS; TURNS; METAL;

D O I：

10.1055/s-0030-1260139

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of diversely functionalized carbohydrate building blocks is of great interest towards the generation of new carbohydrate mimetics. Glycoaminoxy acids are recently developed glycoamino acid analogues with both an aminoxy and a carboxyl group connected to the sugar scaffold. These molecules could be readily used for the synthesis of various glycoconjugates through N-oxy amide or oxime bond, thus providing a potent tool for the design of novel functional carbohydrate mimetics. Here, the efficient synthesis of 2,6-functionalized pyranoid glycoaminoxy acid from commercially available methyl glucopyranoside is reported. The subsequent assembly of this glycoaminoxy acid building unit via N-acylation led successfully to the novel 2,6-linked oligosaccharide mimetics.

引用

页码：2761 / 2766

页数：6

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