Thioglycosides as Potential Glycosyl Donors in Electrochemical Glycosylation Reactions. Part 2: Their Reactivity Toward Sugar Alcohols.

Abstract

Constant potential electrolysis of the glycosyl donors p-methylphenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside (1) and p-methylphenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside (4) in dry acetonitrile in the presence of various primary and secondary sugar alcohols, performed in an undivided cell, gave β-linked disaccharide derivatives selectively in good yields. Oxidative coupling of p-methoxyphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside (2 1) with p-methoxybenzyl 4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside (16) gave selectively the α-linked disaccharide 22 in good yield.