Stereoselective Chemical Synthesis of Sugar Nucleotides via Direct Displacement of Acylated Glycosyl Bromides

The use of Leloir glycosyltransferases to prepare biologically relevant oligosaccharides and glycoconjugates requires access to sugar nucleoside diphosphates, which are notoriously difficult to efficiently synthesize and purify. We report a novel stereoselective route to UDP- and GDP-α-d-mannose as well as UDP- and GDP-β-l-fucose via direct displacement of acylated glycosyl bromides with nucleoside 5‘-diphosphates.