One pot conversion of ketoses into sugar beta-peptides via a Ritter reaction

摘要

alpha -D-Galacto-2-deoxy-oct-3-ulopyranosonic acids can be converted into unnatural glycopeptides via a one pot intramolecular Ritter reaction. Initially, the ketopyranoside reacts under Lewis acid catalyzed conditions with a nitrile (aromatic or aliphatic) to form a glycosylimino anhydride intermediate which can be isolated. Exposure of this intermediate to simple primary amines or amino acids produces novel sugar-beta -peptides. Three different nitriles and three different amines have been used to generate 6 sugar beta -peptides to demonstrate the generality of this reaction. [References: 21]