Počet záznamů: 1
5´-Epimeric 3´-deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses
- 1.0360662 - ÚOCHB 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. E-ISSN 1464-5416
Grant CEP: GA ČR GA202/09/0193; GA ČR GA203/09/1919; GA ČR GA203/09/0820; GA AV ČR KAN200520801; GA MŠMT(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
Počet záznamů: 1