Synthesis and structual assignment of novel 5´-epimeric 3´deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates

0361215 - ÚOCHB 2012 CZ eng C - Konferenční příspěvek (zahraniční konf.)
Petrová, Magdalena - Buděšínský, Miloš - Klepetářová, Blanka - Rosenberg, Ivan
Synthesis and structual assignment of novel 5´-epimeric 3´deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates.
Chemistry of Nucleic Acid Components. 15th Symposium. Praha: Institute of Organic Chemistry and Biochemistry AS CR, v. v. i., 2011 - (Hocek, M.), s. 430-432. Collection Symposium Series, 12. ISBN 978-80-86241-37-1.
[Chemistry of Nucleic Acid Components /15./. Český Krumlov (CZ), 05.06.2011-10.06.2011]
Grant CEP: GA ČR GA203/09/1919; GA ČR GA203/09/0820; GA AV ČR KAN200520801; GA MŠMT(CZ) LC06077
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: 3´,4´-didehydronucleoside C-phophonates * 3´,4´-unsaturated nucleoside * 5´-nucleotide analogue * nucleoside phophonates * Abramov reaction
Kód oboru RIV: CC - Organická chemie

Epimeric 5´-(RS) dialkyl 3-deoxy-3´,4´-didehydro-5´-C-phophonates were prepared by nucleophilic addition of various dialkyl phosphites to 3´-deoxy-3´,4´-didehydronucleoside-5´-aldehydes. Successful separation,crytstallisation 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/11104/0198583