Synthesis and glycosidic coupling reaction of substituted 2,6-dioxabicyco[3.1.1] heptanes: 1,3-anhydro-2-azido-4,6-di-O-benzyl-2-deoxy-β-d-mannopyranose

The title 1,3-anhydro sugar was synthesized from methyl α-d-glucopyranoside. The key intermediate for the synthesis was 3-O-acetyl-2-azido-4,6-di-O-benzyl-2-deoxy-α-d-mannopyranosyl chloride (11) which was transformed into the target compound by ring closure with potassium tert-butoxide.