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Molybdic Acid-Catalyzed Mutual Interconversions of 2-C-(Hydroxymethyl)-D-glucose with D-manno-Hept-2-ulose and 2-C-(Hydroxymethyl)-D-mannose with D-gluco-Hept-2-ulose

Z. Hricovíniová, M. Hricovíni, M. Petrušová, M. Matulová, and L. Petruš

Institute of Chemistry, Slovak Academy of Sciences, SK-842 38 Bratislava

 

Abstract: Nitromethane synthesis with D-fructose followed with the Nef reaction of intermediate 1-deoxy-2-C-hydroxymethylhexitol-1-nitronates afforded 2-C-(hydroxymethyl)-D-glucose and -D-mannose which were separated via their phenylhydrazones and by chromatography on a cation-exchange resin in the Ba2+ form. The treatment of individual branched-chain aldoses with catalytic amount of molybdic acid, i.e. under the conditions of the Bilik reaction afforded thermodynamic equilibrium mixtures of 2-C-(hydroxymethyl)-D-glucose and D-manno-hept-2-ulose in the mole ratio 2 : 55 and of 2-C-(hydroxymethyl)-D-mannose and D-gluco-hept-2-ulose in the ratio 2:23, respectively. The same equilibria were obtained also from the side of hept-2-uloses. Due to easy availability of 2-C-(hydroxymethyl)-D-mannose also from its di-O-isopropylidene derivative the interconversion was advantageously used for one-step synthesis of D-gluco-hept-2-ulose.

Full paper in Portable Document Format: 524a238.pdf

 

Chemical Papers 52 (4) 238–243 (1998)

Tuesday, August 09, 2022

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