Synthesis of vicinal monoamino-dideoxysugars

Abstract

Sequential treatment of methyl 3,4-O-isopropylidene-β-Lerythro-pentopyranosidulose (I) with aqueous NaOH and phenylhydrazine results in elimination of acetone and formation of 2S-methoxytetrahydropyran-3,4-dione 4-phenylhydrazone (III), which has been converted into a 3-amino-3,4-dideoxypentose; and similarly, a 3-amino-3,4,6-trideoxyhexose has been obtained starting with methyl 6-deoxy-3,4-O-isopropylidene-α-L-lyxo-hexo- pyranosidulose (II).