Stereospecific Uncatalyzed α-<i>O</i>-Glycosylation and α-<i>C</i>-Glycosidation by Means of a New <scp>d</scp>-Gulal-Derived α Vinyl Oxirane

Abstract

The reaction of alpha vinyl oxirane 5, prepared through a new route to the d-gulal system, with O-nucleophiles (alcohols and di-O-isopropylidene-alpha-d-monosaccharides) and C-nucleophiles (lithium alkyls) affords, in a completely stereoselective way, the corresponding 2-unsaturated alpha O- and C-glycosides having the same configuration as the starting epoxide.