2-Nitro Thioglycoside Donors:  Versatile Precursors of β-<scp>d</scp>-Glycosides of Aminosugars

Abstract

2-Nitro thioglycosides can be prepared by the Michael addition of thiophenol to 2-nitroglycal derivatives. NIS/TMSOTf activation of these 2-nitro thioglycosides, in the presence of alcohols, rapidly and cleanly led to the desired glycosides in good yield and beta-selectivity. Reduction of the nitro group allowed generation of the corresponding 2-acetamido glycosides.