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Two convergent approaches toward novel carbocyclic C-nucleosides
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SYSNO ASEP 0351443 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Two convergent approaches toward novel carbocyclic C-nucleosides Author(s) Nencka, Radim (UOCHB-X) RID, ORCID
Šála, Michal (UOCHB-X) RID, ORCID
Dejmek, Milan (UOCHB-X) RID, ORCID
Dračínský, Martin (UOCHB-X) RID, ORCID
Holý, Antonín (UOCHB-X)
Hřebabecký, Hubert (UOCHB-X) RID, ORCIDNumber of authors 6 Source Title Synthesis. - : Georg Thieme Verlag - ISSN 0039-7881
-, č. 23 (2010), s. 4119-4130Number of pages 12 s. Language eng - English Country DE - Germany Keywords carbocyclic C-nucleosides ; convergent approach ; uracil ; pyrimidines Subject RIV CC - Organic Chemistry R&D Projects 1M0508 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000284535900028 DOI 10.1055/s-0030-1258271 Annotation Two convergent methodologies for construction of novel carbocyclic C-nucleosides allowing the syntheses of derivatives with uracil heterobase substituted at the position C-5 as well as C-6 were developed. The crucial step of the first methodology was the reaction of (6-chloro-2,4-dimethoxypyrimidin-5-yl)lithium, the nucleobase precursor, with suitable ketones, the carbocyclic pseudosugar precursors. The second approach was based on the copper-catalyzed cross-coupling between magnesiated pyrimidine and appropriate allyl chlorides. These methodologies were applied for the synthesis of novel carbocyclic C-nucleosides bearing cyclohexene or cyclohexane as a pseudosugar. 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 2011
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