Synthesis of 1-deoxy-D-erythro-hexo-2,3-diulose, a major hexose Maillard intermediate

1-Deoxy-D-erythro-hexo-2,3-diulose (1-DG) was prepared by the reaction of ethoxyvinyllithium with an erythronolactone derivative. Characterization by 1H and 13C NMR spectroscopy and NOE difference experiments revealed the 2C5-chair beta-pyranose as the major isomer in solution. Experiments assessing browning and polymerization reactivity proved 1-DG to be a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose.