Preparation of 2-deoxyaldoses from aldose phenylhydrazones

Article abstract of DOI:10.1016/S0008-6215(97)00022-0

Acetylation of D-mannose phenylhydrazone gives acetylated D-arabino-1-phenyl-azo-1-(E)-hexene. Subsequent reduction with sodium borohydride produces 2-deoxy-D-arabino-hexose phenylhydrazone which, on hydrolysis, gives 2-deoxy-D-arabino-hexose. By a similar procedure 2-deoxy-D-lyxo-hexose, 2,6-dideoxy-L-arabino-hexose, and 2-deoxy-D-erythropentose can be prepared from D-galactose, L-rhamnose, and D-arabinose, respectively.