Preparation of bisulphite addition compounds of 5-Amino-5-deoxy-D-xylose

Abstract

Sulphurous acid alone and in admixture with other stronger acids has been used to hydrolyse 5-amino, 5-N-cyclohexylamino, and 5-N-piperidino derivatives of 5-deoxy-l,2-O-isopropylidene-D-xylose. The bisulphite addition compounds of the corresponding amino sugars were thus isolated. Similarly, methyl 5-amino-5-deoxy- 2,3-O-isopropylidene-D-riboside was hydrolysed to yield the bisulphite addition compound of 5-amino-5-deoxy-D-ribose. Treatment of the bisulphite addition compound of 5-amino-5-deoxy-D-xylose with barium hydroxide gave the free amino sugar as a syrup in 96% yield. Removal of bisulphite from the addition compound of 5-X-cyclohexylamino-5-deoxy-D-xylose gave the free sugar in 30% yield together with an amino acid (XVI).