ChemInform Abstract: Synthesis of 1‐Deoxy‐D‐erythro‐hexo‐2,3‐diulose, a Major Hexose Maillard Intermediate.

Abstract

Synthesis of 1-Deoxy-D-erythro-hexo-2,3-diulose, a Major Hexose Maillard Intermediate.-The title compound (V) is synthesized by reaction of the protected erythronolactone (I) with ethoxyvinyllithium (II) followed by transformation of the extremely acid labile vinylether (III) into the carbonyl derivative (IV) which is deprotected under mild controllable conditions. The major isomer of the title compound in solution adopts the 2 C 5 -chair conformation. Compound (V) is a much more potent protein modifier than 3-deoxy-D-erythro-hexos-2-ulose. -(GLOMB, MARCUS A.; PFAHLER, CHRISTOPH; Carbohydr. Res. 329 (2000) 3, 515-523; Inst.