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  • Title: Highly stereoselective synthesis and structural characterization of new amino sugar derivatives.
    Author: Liu FW, Yan L, Zhang JY, Liu HM.
    Journal: Carbohydr Res; 2006 Feb 27; 341(3):332-8. PubMed ID: 16343461.
    Abstract:
    2-C-Nitroalkyl-1,4:3,6-dianhydromannitols were synthesized via a Henry reaction of nitroalkyls with 1,4:3,6-dianhydrofructose. Catalytic hydrogenation then afforded the corresponding vicinal amino alcohols. Oximation of 1,4:3,6-dianhydrofructose with hydroxylamine, followed by hydrogenation, gave 2-amino-1,4:3,6-dianhydro-2-deoxymannitol. All compounds were elucidated by their HRMS, 1H NMR, 13C NMR, and IR spectra. The absolute configurations of the amino sugar derivatives were confirmed by single-crystal X-ray analysis or NOESY spectral studies. The possible mechanism for hydrogenation of the nitro 2-C-nitroalkyl sugar is proposed. The conformations of the fused furan rings of nitro and amino sugar derivatives are presented.
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