Glycosylation Using Methylthioglycosides ofN-Acetylneuraminic Acid and Dimethyl(Methylthio)Sulfonium Triflate

Abstract
Recently, great interest has been focussed on the synthesis of oligosaccharides containing N-acetylneuraminic acid (Neu5Ac) because of its important roles in a variety of biological recognitions.2 However, many difficulties in the synthesis of naturally occurring α-glycosides still remained.3 We have recently reported the stereo-selective synthesis of a series of α- and β-2-thio-neuraminyl glycosides.1-4 In the meantime, the utility of thioglycosides in oligosaccharide synthesis has been widely developed.5 Particularly noteworthy is the dimethyl(methylthio)sulfonium triflate (DMTST) promoted glyco-sylation method5k.1 because excellent yields are achieved due to the high thiophilicity of this reagent.