Carboxymethyl glycoside lactone(CMGL) synthons:Scope of the method and preliminary results on step growth polymerization of α-azide-ω-alkyne glycomonomers

作     者：CHAMBERT Stéphane BERNARD Julien FLEURY Etienne QUENEAU Yves 

作者机构：INSA-LyonLaboratoire de Chimie Organique et Bioorganique Bat.J.Verne20 Avenue A.Einstein69621 Villeurbanne CedexFrance ICBMSInstitut de Chimie et de Biochimie Moléculaires et SupramoléculairesUMR5246 CNRS université de Lyon université Lyon 1 INSA-Lyon CPE-Lyon Bat.Curien43 Bd du 11 Novembre 1918F 69622 VilleurbanneFrance INSA-LYONIMP1ngénierie des Matériaux Polymères UMR5223 université de Lyonuniversité Claude Bernard Lyon 1F-69621 Villeurbanne CedexFrance 

出 版 物：《Science China Chemistry》 (中国科学（化学英文版）)

年 卷 期：2010年第53卷第9期

页      面：1880-1887页

核心收录：

学科分类：081704[工学-应用化学] 07[理学] 08[工学] 0817[工学-化学工程与技术] 070305[理学-高分子化学与物理] 080501[工学-材料物理与化学] 0805[工学-材料科学与工程（可授工学、理学学位）] 0703[理学-化学] 

基　　金：Financial support from CNRS and MESER is gratefully acknowledged  as well as a fellowship from Chinese Scholarship Council to CHEN Jie 

主　　题：carbohydrates glycopolymers lactones click chemistry step growth polymerization glycoconjugates azides alkynes Huisgen cycloaddition 

摘      要：Carboxymethyl glycoside lactones(CMGLs) are bicyclic synthons which open readily for accessing new types of pseudo-glycoconjugates,such as sugar-amino acid hybrids,neoglycolipids,pseudodisaccharides,and membrane imaging *** lactone opening,free OH-2 is available for further functionalization,leading to 1,2-bisfunctionalized *** strategy is illustrated herein with new polymerizable systems of the AB type bearing both azide and alkyne functions prepared from α or β gluco-CMGL *** the reaction of lactones with propargylamine,an azido group was introduced by two different sequences leading to either the 2-manno-azido or the 6-gluco-azido *** capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition(CuAAC) and generate glycopolytriazoles was evidenced.