Chemoselective activation of ethyl vs. phenyl thioglycosides: one-pot synthesis of oligosaccharides

Abstract

Ethyl and phenyl thioglycosides are the two most common types of thioglycoside donors in carbohydrate chemistry. However, the chemoselective activation of ethyl vs. phenyl thioglycosides is very rare in the literature. In this work, ethyl thioglycosides could be readily activated with an N-trifluoromethylthiosaccharin/TMSOTf system in the presence of phenyl thioglycosides carrying the same or even more armed protecting group pattern. Both armed and disarmed thioglycosides exhibited high chemoselectivity towards the promoter system. Chemoselective glycosylation was subsequently applied to one-pot synthesis, thus providing an efficient means to oligosaccharides.