Synthesis of 4-substituted-2-acetamido-2,4-dideoxy-mannopyranoses using 1,6-anhydro sugar chemistry

The introduction of nitrogen, sulfur, and bromine substituents at C-4 of 2-acetamido-2-deoxy-d-mannopyranose has been readily achieved through opening of the 3,4-epoxide of 2-acetamido-1,6:3,4-dianhydro-2-deoxy-β-d-talopyranose.