SYNTHESIS OF 2-DEOXY-D-arabino-HEXITOL AND ITS OXIDATION TO 5-DEOXY-D-threo-HEXULOSE ("5-DEOXY-D-FRUCTOSE") USING IMMOBILIZED CELLS OF Gluconobacter oxydans

Article abstract of DOI:10.1016/S0008-6215(00)90096-X

2-Deoxy-D-arabino-hexitol (6) was obtained by borohydride reduction of 2-deoxy-D-arabino-hexose (5).The synthesis of 5, starting from 2,3:4,5-di-O-isopropylidene-D-arabinitol (1), was achieved by one-carbon chain-elongation involving formylation of the Grignard reagent derived from 1-bromo-1-deoxy-2,3:4,5-di-O-isopropylidene-D-arabinitol (2), using lithium formate, followed by hydrolytic removal of the isopropylidene groups.Immobilized cells of Gluconobacter oxydans (ATCC) 15178) selectively oxidized 6 to give 5-deoxy-D-threo-hexulose (7) in 65percent yield (-9percent overall yield from 1).