A novel synthesis of β- d-mannopyranosyl azide by phase transfer catalysis

Abstract

A simple stereoselective synthesis of per- O-benzoyl-β- d-mannopyranosyl azide from per- O-benzoyl-α- d-mannopyranosyl bromide using phase transfer catalysis was developed. The stereochemistry at C-1 of the anomeric O-benzoylated α- and β- d-mannopyranosyl azides was unambiguously established using 2D NOESY NMR spectroscopy. Pure deprotected β- d-mannopyranosyl azide was prepared by debenzoylation with sodium methoxide in methanol.