Synthesis of Some Glycosylated Derivatives of 2-Deoxy-2-fluoro-β-laminaribiosyl Fluoride: Another Success for Glycosynthases

Abstract

The synthesis of 4,6-di-O-acetyl-2-deoxy-2-fluoro-3-O-(tetra-O-acetyl-β-d-glucopyranosyl)-β-d-glucosyl fluoride is described. Upon deacetylation and treatment with α-d-glucopyranosyl fluoride in the presence of a glycosynthase, three products, all 2-deoxy-2-fluoro-β-glycosyl fluorides, could be isolated: a trisaccharide, a tetrasaccharide, and a pentasaccharide. An attempt to convert a trisaccharide glycal into a related difluoride, employing Selectfluor, is also reported.