α-Selective glycosidation of d-tagatofuranose with a 3,4-O-isopropylidene protection

Abstract

An α-selective glycosidation reaction of d-tagatofuranose was successfully achieved using 3,4-O-isopropylidene-protected d-tagatofuranose as a glycosyl donor. A variety of glycosyl acceptors, including primary, secondary, and β-amino alcohols, and carbohydrates, can be used for this d-tagatofuranosidation reaction with complete α-selectivities and good yields (57–83%). The stereochemistries at the anomeric positions were determined by nuclear Overhauser effect spectroscopic correlations, as well as comparison of the chemical shifts in the 13C NMR spectra.