Fluoropyridyl Sugars – Masked Imidate Glycosyl Donors that Display Reactivity, Selectivity, and Stability

Abstract

Fluoropyridyl glycosides, synthesized from the corresponding glycosyl bromides, are shown to be excellent donors in glycosylation reactions. Both armed and disarmed donors were prepared and reacted smoothly with a series of glycosyl acceptors. Coupling proceeded in high yields, with activation of the donor achieved using a range of promoters, and also displayed unusually high selectivity. In addition these novel systems offer the potential for introducing a series of glycosyl donors with ‘tunable reactivity’.