Benzene-1,3-disulfonyl Fluoride Mediated Synthesis of Glycosyl Fluorides from Glycosyl Hemiacetals.

Abstract

We developed an efficient method for synthesizing glycosyl fluorides from glycosyl hemiacetals using benzene-1,3-disulfonyl fluoride (S2) as the fluorinating agent in combination with the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under mild conditions. This approach enabled the successful synthesis of 17 glycosyl fluorides with various functional groups, including disaccharides and deoxysulfates, with yields of up to 99%. The utility of these synthesized glycosyl fluorides was further demonstrated in the synthesis of important O- and C-glycosides.