Synthesis of 2-acetamido-2-deoxy-D-gulose, 2-acetamido-2-deoxy-D-idose, and 2-deoxy-D-xylo-hexose from 3,4,5,6-tetraacetoxy-D-xylo-1-nitro-1-hexene

3,4,5,6-Tetraacetoxy- D -xylo-1-nitro-1-hexene with methanolic ammonia afforded a mixture of 2-acetamido-1,2-dideoxy-1-nitro- D -gulitol and 2-acetamido-1,2-dideoxy-1-nitro- D -iditol which were converted via a Nef reaction to 2-acetamido-2-deoxy- D -gulose and 2-acetamido-2-deoxy- D -idose.Reduction of 3,4,5,6-tetraacetoxy- D -xylo-1-nitro-1-hexene afforded 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-1-nitro- D -xylo-hexitol which was converted via the Nef reaction to 2-deoxy- D -xylo-hexose.