The nitrous acid deamination of methyl 4-amino-4-deoxy-2,3-O-isopropylidene-α-L-talo- and -mannopyranosides

Abstract
Deamination of the L-talo-amine (I) with sodium nitrite in 90% acetic acid afforded the L-mannopyranosides (III) and (IV), whereas similar deamination of the L-manno-amine (V) gave (III), (IV), and rearrangement products (VIII) and (IX) possessing the D-allo-configuration.