Regio- and Stereoselective Synthesis of Thioglycosides from 4,5-Diphenyl- and 3,4,5-Triphenylimidazole-2-thione

Abstract

Six new thioglycosides incorporating the 4,5-diphenyl- and 3,4,5-triphenylimidazole moiety have been successfully synthesized under both conventional and microwave conditions by reaction of the corresponding thiones with aceto-bromosugars in presence of triethylamine as base. Attempted preparation of the bis(glycosyl) derivatives from 4,5-diphenylimidazole-2-thione in the presence of different bases was unsuccessful. Evaluation of the glycosylthioimidazoles as disarmed donors has been investigated using different promoters; NBS/TMSOTf has been found to be an effective promoter for the activation of the anomeric center towards glycosylation reaction.

Keywords:

• 4,5-Diphenylimidazole
• glycosylation
• microwave irradiation
• oligosaccharide
• thioglycosides
• 3,4,5-triphenylimidazole