The deamination of pyranose amines. Part I. Equatorial amines

Abstract

The deamination of methyl 4-amino-4-deoxy-α-D-glucopyranoside with nitrous acid gives methyl α-D-glucopyranoside (major product), methyl β-L-altrofuranoside, 4,5-anhydro-D-galactose, and methyl 3-deoxy-3-formyl-α-D-xylofuranoside. Deamination of 2-amino-1,5-anhydro-2-deoxy-D-glucitol gives 1,5-anhydro-D-glucitol as the major product. Participation of the ring oxygen atom dominates the reactions of these and related compounds, in which the equatorial amino group is at C-2 or C-4.