Two Syntheses of 3-Azido-3-deoxy-D-mannose

Abstract

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α-D-mannopyranose (10) was prepared from 1,6:3,4-dianhydro-β-D-altropyranose (8) by a nucelophilic oxirane-ring opening promoted by azide ions followed by acetolysis. Alternatively, regioselective enzymatic de-O-acetylation of 1,6-anhydro-2,4-di-O-acetyl..3-azido-3-deoxy-β-D-glucopyranose (1) gave isomers 2 and 3. The latter was reacted with trifluoromethanesulfonic acid anhydride/sodium acetate to give 1,6-anhydro-2,4-di-O-acetyl-3-azido-3-deoxy- β-D-mannopyranose (9).