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  • Title: Access to ring-expanded analogues of 2-amino sugars.
    Author: Saha J, Peczuh MW.
    Journal: Org Lett; 2009 Oct 01; 11(19):4482-4. PubMed ID: 19722606.
    Abstract:
    Ring-expanded 2-N-acetylamino sugar analogs of D-glucose, D-galactose, and D-mannose have been prepared by a new synthetic route. Aspects of the highly substituted alpha-amino aldehyde intermediates made them central to the approach. First, they were accessed via diastereoselective addition of a vinyl Grignard onto protected glycosyl amines. Also, the sterics of the bis-protected amine favored the formation of only one glycoside anomer. The new analogues reported here should prove useful in the development of tools to investigate the role of 2-amino sugars in biology.
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