Synthesis of 2,3-diazido-2,3-dideoxy-β-d-mannosides and 2,3-diazido-2,3-dideoxy-β-d-mannuronic acid via stereoselective anomeric O-alkylation.

Stereoselective synthesis of 2,3-diazido-2,3-dideoxy-β-d-mannosides has been accomplished via Cs(2)CO(3)-mediated anomeric O-alkylation of 2,3-diazido-2,3-dideoxy-β-d-mannoses with primary electrophiles. Selective oxidation of the C6 primary alcohol of the 2,3-diazido-2,3-dideoxy-β-d-mannoside successfully produced corresponding 2,3-diazido-2,3-dideoxy-β-d-mannuronic acid.