SYNTHESIS OF A DERIVATIVE OF 1-DEOXY-D-erythro-2,3-HEXODIULOSE AND ITS CONVERSION INTO NONENZYMIC BROWNING PRODUCTS

Article abstract of DOI:10.1016/0008-6215(83)88110-5

A new synthesis of 1-deoxy-4,5-O-isopropylidene-D-erythro-2,3-hexodiulose (5), a stable derivative of the elusive 1-deoxy-D-erythro-2,3-hexodiulose (6), starting from 3,6-anhydro-4,5-O-isopropylidene-D-mannitol (1) is described.Acid hydrolysis of 5 produced 6, which without isolation was treated with piperidine acetate to yield piperidino-hexose-reductone (7) and 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (8).A third component in the reaction mixture has been tentatively assigned from mass-spectroscopic data the structure 4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone (9).