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General and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups

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    SYSNO ASEP0364189
    Document TypeJ - Journal Article
    R&D Document TypeJournal Article
    Subsidiary JČlánek ve WOS
    TitleGeneral and Modular Synthesis of Isomeric 5-Substituted Pyridin-2-yl and 6-Substituted Pyridin-3-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Hetaryl, Amino, Carbamoyl, and Hydroxy Groups
    Author(s) Štefko, Martin (UOCHB-X)
    Slavětínská, Lenka (UOCHB-X) RID
    Klepetářová, Blanka (UOCHB-X) RID, ORCID
    Hocek, Michal (UOCHB-X) RID, ORCID
    Number of authors4
    Source TitleJournal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
    Roč. 76, č. 16 (2011), s. 6619-6635
    Number of pages17 s.
    Languageeng - English
    CountryUS - United States
    Keywordsnucleosides ; palladium-catalyzed amination ; C-2'-deoxyribonucleosides ; cytidine ; benzene
    Subject RIVCC - Organic Chemistry
    R&D ProjectsLC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
    IAA400550902 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
    CEZAV0Z40550506 - UOCHB-X (2005-2011)
    UT WOS000293759000016
    DOI10.1021/jo200949c
    AnnotationA general modular and practical methodology for preparation of diverse 5-substituted pyridin-2-yl and 6-substituted pyridin-3-yl C-ribonucleosides was developed. Regioselective lithiation of 2,5-dibromopyridine proceeded at the position 5- or 2- depending on the solvent and the resulting bromopyridyl lithium species underwent additions to protected ribonolactone and further transformations to hemiketals that were diastereoselectively reduced to give either 5-bromopyridine-2-yl or 6-bromopyridine-3-yl silyl-protected C-ribonucleosides. These intermediates were then subjected to a series of cross-coupling reactions, aminations, aminocarbonylations and hydroxylations to give a series of protected 1beta-(5-alkyl-, 5-aryl-, 5-amino- 5-carbamoyl and 5-hydroxypyridin-2-yl)-C-ribonucleosides and beta-(6-alkyl-, 6-aryl-, 6-amino- 6-carbamoyl and 6-hydroxypyridin-3-yl)-C-ribonucleosides. Deprotection of silylated nucleosides by Et3N.3HF, TBAF or TFA gave a series of free C-nucleosides.
    WorkplaceInstitute of Organic Chemistry and Biochemistry
    Contactasep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
    Year of Publishing2012
Number of the records: 1  

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