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Stereoselective Synthesis of α- and β-Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides

Authors

  • Dr. Filippo Nisic,

    1. Universitá degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano (Italy)
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  • Gaetano Speciale,

    1. Universitá degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano (Italy)
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  • Prof. Dr. Anna Bernardi

    Corresponding author
    1. Universitá degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano (Italy)
    • Universitá degli Studi di Milano, Dipartimento di Chimica Organica e Industriale, via Venezian 21, 20133 Milano (Italy)
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Abstract

A highly stereoselective synthesis of α- or β-glycofuranosyl amides based on the traceless Staudinger ligation of glycofuranosyl azides of the galacto, ribo, and arabino series with 2-diphenylphosphanyl-phenyl esters has been developed. Both α- and β-isomers can be obtained with excellent selectivity from a common, easily available precursor. The process does not depend on the anomeric configuration of the starting azide but appears to be controlled by the C2 configuration and by the protection/deprotection state of the substrates. A mechanistic interpretation of the results, supported by 31P NMR experiments, is offered and merged with our previous mechanistic analysis of pyranosyl azide ligation reactions.

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