An electrochemical synthesis of methyl α isomaltoside

A novel approach has been developed for the synthesis of methyl α-isomaltoside (10), comprising, as the first step, electrochemical conversion of the hydroxyl groups of methyl α-d-glucopyranoside into the corresponding anions. The anions subsequently react with tetra-O-acetyl-α-d-glucopyranosyl bromide to give methyl 2′,3′,4′,6′-tetra-O-acetyl-α-isomaltoside (8) as the main product, O-deacetylation of which affords 10. The glycosidation proceeds under complete stereochemical control.