Počet záznamů: 1

Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses

  1. 1.
    0343244 - UCHP-M 2011 RIV US eng J - Článek v odborném periodiku
    Karban, Jindřich - Sýkora, Jan - Kroutil, J. - Císařová, I. - Padělková, Z. - Buděšínský, Miloš
    Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses.
    Journal of Organic Chemistry. Roč. 75, č. 10 (2010), s. 3443-3446 ISSN 0022-3263
    Grant CEP: GA AV ČR IAA400720703; GA AV ČR IAA400720706
    Výzkumný záměr: CEZ:AV0Z40720504; CEZ:AV0Z40550506
    Klíčová slova: fluorinated hexopyranoses * synthesis * experiments
    Kód oboru RIV: CF - Fyzikální chemie a teoretická chemie
    Impakt faktor: 4.002, rok: 2010

    Fluorinated hexopyranoses are important synthetic targets because of their utilization as probes in enzymology, medicine and structure - reactivity studies. We have prepared a full series of 1,6-anhydro-2,3,4-deoxy-4-fluoro-2,3-epimino-β-D-hexopyranoses. The key step was reaction of trans-2,3-azidosulfonates possessing a free C-4 hydroxyl with DAST and subsequent LiAlH4 reduction. Nucleophilic displacement of the hydroxyl activated by DAST proceeded without rearrangement and with moderate to good yields. A convenient synthesis of D-manno epimine from a readily available 3-benzylamino derivative was also developed.
    Trvalý link: http://hdl.handle.net/11104/0185763