Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate

Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide different polycholesterylated products. [Display omitted] •Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide glycoconjugates.•The cholesterylation reactions are completely stereoselective.•Polyol reactions yield mono-, di-, tri-, or tetra-cholesterylated products. Electrochemical cholesterylation of various sugars with cholesteryl diphenylphosphate was studied. The reaction afforded mono-, di-, tri-, and tetra-cholesterylated products using equivalent amounts of the reagent. The reactions turned out to be completely stereoselective with respect to both sugar and steroid but only partially regioselective – primary and anomeric hydroxyl groups in sugars were the most reactive ones while no substantial differences in reactivity was found for different secondary hydroxyl groups.