Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents  

作　　者：RANOUX Adeline LEMIEGRE Loc BENVEGNU Thierry 

机构地区：[1]Ecole Nationale Supérieure de Chimie de Rennes,CNRS UMR 6226,Université Européenne de Bretagne

出　　处：《Science China Chemistry》2010年第9期1957-1962,共6页中国科学（化学英文版）

基　　金：the ANRT (Association Nationale de la Recherche et de la Technologie) and the Armor Protéines Company for a grant to AR and for funding

摘　　要：This work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di-or mono-saccharides.A Horner-Wadsworth-Emmons/Michael addition/Barbier allylation sequence led to C-glycosides that exhibit hydrotropic properties.The hydrotropic and solubilizing properties of these homoallylic alcohols including a β-C-glycoside moiety as well as additional β-C-glycosidic ketones with a short(C7) alkyl chain are also described and compared with those of commercial O-glucoside references.This work presents expeditious synthesis of C-glycoside amphiphiles in aqueous media from unprotected di-or mono-saccharides.A Horner-Wadsworth-Emmons/Michael addition/Barbier allylation sequence led to C-glycosides that exhibit hydrotropic properties.The hydrotropic and solubilizing properties of these homoallylic alcohols including a β-C-glycoside moiety as well as additional β-C-glycosidic ketones with a short(C7) alkyl chain are also described and compared with those of commercial O-glucoside references.

关 键 词：C-GLYCOSIDE amphiphiles Horner-Wadsworth-Emmons reaction Barbier ALLYLATION green CHEMISTRY HYDROTROPES 

分 类 号：O621.25[理学—有机化学]