1,6-Anhydro-4-deoxy-4-diazo-2,3-O-isopropylidene-β-D-lyxo-hexopyranose, a stable diazo-sugar from a keto-sugar precursor

Abstract

The keto-sugar derivative 1,6-anhydro-2,3-O-isopropylidene-β-D-lyxo-hexopyranos-4-ulose (I) has been converted by way of the sodium salt of its 2,4,5-trichlorobenzenesulphonylhydrazone into 1,6-anhydro-4-deoxy-4-diazo-2,3-O-isopropylidene-β-D-lyxo-hexopyranose (IV); this diazo-sugar can be sublimed without decomposition and derivatives of this type are of potential value in synthesis of branched-chain and other modified sugars.