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Nitromethane Addition to Aldoses Promoted by Strongly Basic Anion-Exchange Resin in the OH- Form

E. Lattová, M. Petrušová, A. Gáplovský, and L. Petruš

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


Abstract: 1-Deoxy-1-nitroalditols can be readily obtained by one-pot reaction of aldoses with nitromethane in aqueous methanol in the presence of a strongly basic anion-exchange resin in the OH- form and subsequent transformation of the resin into the HCO3- form with dry ice. All D-pentoses and six available D-hexoses gave moderate to high conversions (48-91 %) to the nitroaldol products, mostly both epimeric 1-deoxy-1-nitroalditols, in some cases accompanied by tautomeric 2,5- and 2,6-anhydro-1-deoxy-1-nitroalditols . Both types of the strongly basic anion-exchange resins used, R-CH2N+Me3 OH- and R-CH2N+Me2(CH2CH2OH) OH- showed comparable catalytic efficiency. Examples of preparation of 1-deoxy-1-nitro-L-mannitol and -L-glucitol as well as L-mannose and L-glucose show a practical application of the procedure.

Full paper in Portable Document Format: 502a97.pdf


Chemical Papers 50 (2) 97–100 (1996)

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