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 

机构地区：[1]INSA-Lyon,Laboratoire de Chimie Organique et Bioorganique [2]Bat.J.Verne,20 Avenue A.Einstein,69621 Villeurbanne Cedex,France [3]ICBMS,Institut de Chimie et de Biochimie Moléculaires et Supramoléculaires,UMR5246 [4]CNRS [5]université de Lyon [6]université Lyon 1 [7]INSA-Lyon [8]CPE-Lyon [9]Bat.Curien,43 Bd du 11 Novembre 1918,F 69622 Villeurbanne,France [10]INSA-LYON,IMP,1ngénierie des Matériaux Polymères [11]UMR5223 [12]université de Lyon,université Claude Bernard Lyon 1,F-69621 Villeurbanne Cedex,France

出　　处：《Science China Chemistry》2010年第9期1880-1887,共8页中国科学（化学英文版）

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

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 systems.After lactone opening,free OH-2 is available for further functionalization,leading to 1,2-bisfunctionalized derivatives.This 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 synthons.After 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 products.The capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition(CuAAC) and generate glycopolytriazoles was evidenced.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 systems.After lactone opening,free OH-2 is available for further functionalization,leading to 1,2-bisfunctionalized derivatives.This 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 synthons.After 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 products.The capability of these AB monomers to undergo step growth polymerization through copper(I) catalyzed alkyne-azide cycloaddition(CuAAC) and generate glycopolytriazoles was evidenced.

关 键 词：carbohydrates GLYCOPOLYMERS lactones click chemistry STEP GROWTH POLYMERIZATION GLYCOCONJUGATES azides alkynes Huisgen cycloaddition 

分 类 号：O631[理学—高分子化学]