SYNTHESIS OF 3-AMINO-2,3-DIDEOXY-D-lyxo-HEXOSE

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Abstract
Catalytic hydrogenation of methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-threo-hexo-pyranos-2-enide (I) afforded methyl 4,6-O-benzylidene-2,3-dideoxy-3-nitro-β-D-lyxo-hexo-pyranoside (II). Acid debenzylidenation and further hydrogenation gave in turn methyl 2,3-dideoxy-3-nitro-β-D-lyxo-hexopyranoside (III) and the corresponding amine hydrochloride (IV). Several crystalline derivatives of IV were prepared, and the configuration at C-3 was proved by degradation of the N-benzoate (VII) to N-benzoyl-D-aspartic acid. The title compound (V) was obtained as a chromatographically homogeneous sirup.Some methyl 3-deoxy-3-nitro-β-L-hexopyranosides were prepared for potential use as starting materials in analogous syntheses in the L-series.