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5´-Epimeric 3´-deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses
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SYSNO ASEP 0360662 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title 5´-Epimeric 3´-deoxy-3´,4´-didehydronucleoside-5´-C-phosphonates: synthesis and structural assignment by NMR and X-ray analyses Author(s) Petrová, Magdalena (UOCHB-X) RID
Buděšínský, Miloš (UOCHB-X) RID, ORCID
Klepetářová, Blanka (UOCHB-X) RID, ORCID
Rosenberg, Ivan (UOCHB-X) RID, ORCIDNumber of authors 4 Source Title Tetrahedron. - : Elsevier - ISSN 0040-4020
Roč. 67, č. 23 (2011), s. 4227-4235Number of pages 9 s. Language eng - English Country GB - United Kingdom Keywords Abramov reaction ; hydroxy phosphonates ; 3´,4´-didehydronucleoside C-phosphonates ; gamma-gauche interaction Subject RIV CC - Organic Chemistry R&D Projects GA202/09/0193 GA ČR - Czech Science Foundation (CSF) GA203/09/1919 GA ČR - Czech Science Foundation (CSF) GA203/09/0820 GA ČR - Czech Science Foundation (CSF) KAN200520801 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) LC06077 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000291371900013 DOI 10.1016/j.tet.2011.04.037 Annotation 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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Year of Publishing 2012
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