Specific Features of Phase Transfer Catalytic Glycosylation of 2-Mercaptobenzimidazole

Abstract

The reaction of 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl chloride with 2‑mercaptobenzimidazole under conditions of the phase transfer catalysis was studied and specific features of the phase transfer process were evaluated. It was found that the corresponding N- and S-β-D-glucosaminides were the major glucosaminylation products. Glucosaminylation of 2-mercaptobenzimidazole in an anhydrous methylene chloride–sodium hydride phase transfer catalytic system was shown to proceed regiospecifically. The structures of the synthesized compounds were characterized using 1H NMR spectroscopy and mass spectrometry.