Synthesis of 2-amino-2-deoxy-D-allose, 2-amino-2-deoxy-D-altrose, and 2-deoxy-D-ribo-hexose from 3,4,5,6-tetraacetoxy-D-ribo-1-nitro-1-hexene

Abstract

3,4,5,6-Tetraacetoxy-D-ribo-1-nitro-1-hexene with methanolic ammonia afforded a mixture of 2-acetamido-1,2-dideoxy-1-nitro-D-allitol and 2-acetamido-1,2-dideoxy-1-nitro-D-altritol, which were converted via the Nef reaction to 2-acetamido-2-deoxy-D-allose and 2-acetamido-2-deoxy-D-altrose. 2-Amino-2-deoxy-D-allose hydrochloride and 2-amino-2-deoxy-D-altrose hydrochloride were obtained from the 2-acetamido-2-deoxy-glycoses.Reduction of 3,4,5,6-tetraacetoxy-D-ribo-1-nitro-1-hexene afforded 3,4,5,6-tetra-O-acetyl-1,2-dideoxy-1-nitro-D-ribo-hexitol which was converted via the Nef reaction to 2-deoxy-D-ribo-hexose.