Synthesis and electrochemical behaviour of new electroreducible amphiphilic saccharide derivatives

Abstract

mes a`Inte reü t 6504), a Equipe et Electroanalyse Bioorganique and b Equipe de Chimie dÏElectrosynthe`se Organique Structurale,

Electrochemical Reduction in an Aprotic Medium of New Functionalized Amphiphilic Molecules Derived from Sugars: Stereoselective Pinacolization and an Example of a Glycosidic Carbon-Oxygen Bond Cleavage

“…In a previous paper, [9] we described the syntheses of the glucopyranosides 1 and 2 according to the Schmidt glycosylation reaction. [13] The synthesis of the 1-O-[8-(4-acetylphenoxy)octyl] β--glucofuranosidurono-6,3-lactone 3 was performed in dry tetrahydrofuran in a single condensation Scheme 1.…”

“…[9] In the present article, we report the results of the macroscale electrolyses of glycosidic amphiphilic molecules derived from -glucose 1 and 2 or from -glucurone 3 performed in an aprotic medium. In the latter case, 3, the electrolyses were achieved in the absence or in the presence of a proton donor.…”

Electrochemical behaviour of new electroreducible amphiphilic saccharide derivatives II: Electroreduction in protic media

“…In a previous paper, we have described the electrochemical behaviour of these surfactant molecules and their adsorption mode at the HgÈelectrolyte solution interface. 5 We have recently presented the results of macroscale electrolyses in an aprotic medium of ketones derived from D-glucose (GluAcO3, GluAcO8) and Dglucurone (LacAcO8). 6 In the present paper, we discuss the results of macroscale electrolyses of this type of compounds, performed in protic media, hydroalcoholic and aqueous solu-tions at pH 3 and pH 9, with the help of molecular dynamics calculation.…”