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Synthesis 2011(17): 2761-2766  
DOI: 10.1055/s-0030-1260139
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Zhuo Songa, Xiao-Peng Hea,b, Guo-Rong Chen*a, Juan Xie*b
a Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China
Fax: +86(21)64252758; e-Mail: mrs_guorongchen@ecust.edu.cn;
b PPSM, ENS Cachan, CNRS, 61 Ave President Wilson, 94230 Cachan, France
Fax: +33(1)47402454; e-Mail: joanne.xie@ens-cachan.fr;
Further Information

Publication History

Received 22 April 2011
Publication Date:
28 July 2011 (online)

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Abstract

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.

Key words

aminoxy acids - glycoaminoxy acids - oligosaccharide mimetics - carbohydrates - oligomers

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