Počet záznamů: 1

5´-Epimeric 3´-deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses

  1. 1.
    0360662 - UOCHB-X 2012 RIV GB eng J - Článek v odborném periodiku
    Petrová, Magdalena - Buděšínský, Miloš - Klepetářová, Blanka - Rosenberg, Ivan
    5´-Epimeric 3´-deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses.
    Tetrahedron. Roč. 67, č. 23 (2011), s. 4227-4235 ISSN 0040-4020
    Grant CEP: GA ČR GA202/09/0193; GA ČR GA203/09/1919; GA ČR GA203/09/0820; GA AV ČR KAN200520801; GA MŠk(CZ) LC06077
    Výzkumný záměr: CEZ:AV0Z40550506
    Klíčová slova: Abramov reaction * hydroxy phosphonates * 3´,4´-didehydronucleoside C-phosphonates * gamma-gauche interaction
    Kód oboru RIV: CC - Organická chemie
    Impakt faktor: 3.025, rok: 2011

    Epimeric 5'-(RS) dialkyl 3-deoxy-3',4'-didehydro-5'-C-phosphonates were prepared by nucleophilic addition of various dialkyl phosphites to 3'-deoxy-3',4'-didehydronucleoside-5'-aldehydes. Whereas direct NMR configuration assignment for the C5' atom bearing the phosphoryl and hydroxy groups using the J (P,H4') and J (H5',H4') coupling constants is impossible due to the absence of the H4' atom, successful separation, crystallisation and X-ray analysis of a pair of epimeric 5'-C-phosphonates, followed by correlation with a series of NMR parameters, led to efficacious configuration assignment of individual epimers in the mixtures.
    Trvalý link: http://hdl.handle.net/11104/0198162