Electrochemical cholesterylation of sugars with cholesteryl diphenylphosphate

- 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.

Electrochemical reactions of sugars with cholesteryl diphenylphosphate provide different polycholesterylated products.77