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

Adeline Ranoux (1) , Loïc Lemiègre (1) , Thierry Benvegnu (1)

1 ISCR - Institut des Sciences Chimiques de Rennes

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.

Mots clés: C-glycoside amphiphiles; Horner-Wadsworth-Emmons reaction; Barbier allylation; green chemistry; hydrotropes

Domaines: Chimie organique

Adeline Ranoux, Loïc Lemiègre, Thierry Benvegnu. Synthesis and evaluation of C-glycosides as hydrotropes and solubilizing agents. Science China Chemistry, 2010, 53 (9), pp.1957-1962. ⟨10.1007/s11426-010-4055-3⟩. ⟨hal-00757741⟩