Highly Reactive Glycosylation with 1-O-(Methylthio)thiocarbonyl Glycosyl Donors under Acidic to Neutral Reaction Conditions

Abstract

In this study, we have successfully developed a glycosylation method using 1-O-(methylthio)thiocarbonyl−glycoses as donors. Such xanthate donors are easily accessible and shelf-stable. The glycosylation reaction could be promoted by cations (acidic to neutral conditions) under mild conditions, exhibiting a reactivity intermediate between that with glycosyl trichloroacetimidate as the donor and that with thioglycoside as the donor. This methodology tolerates both "armed" and "disarmed" glycosyl donors, as well as various sugar acceptors, and affords the corresponding glycosides in good to excellent yields. Based on the relative higher reactivity of such xanthate donors than thioglycoside donors under the same glycosylation conditions, a trisaccharide was further synthesized in a one-pot glycosylation strategy.