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  • Title: A novel approach to the synthesis of amino-sugars. Routes to selectively protected 3-amino-3-deoxy-aldopentoses based on pyridinium salt photochemistry.
    Author: Lu H, Su Z, Song L, Mariano PS.
    Journal: J Org Chem; 2002 May 17; 67(10):3525-8. PubMed ID: 12003573.
    Abstract:
    A new approach for the synthesis of selectively blocked 3-amino-3-deoxyaldopentoses is presented. The strategy is based on employment of a pyridinium salt photocyclization-aziridine ring-opening sequence to prepare stereochemically defined, enantiomerically enriched aminocyclopentendiol derivatives. Ring-opening reactions transform these substances into terminally differentiated aminopolyols, which serve as precursors to the target amino-aldopentoses. The utility of this strategy is demonstrated by its application to the syntheses of protected derivatives of D- and L-3-amino-3-deoxyxylose, L-3-amino-3-deoxyarabinose, and a late-stage intermediate in a potential route to N-acetylneuraminic acid.
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