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A General and Efficient Synthesis of Pyridin-2-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Amino and Carbamoyl Groups in Position 6
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SYSNO ASEP 0342342 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title A General and Efficient Synthesis of Pyridin-2-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Amino and Carbamoyl Groups in Position 6 Author(s) Štefko, Martin (UOCHB-X)
Slavětínská, Lenka (UOCHB-X) RID
Klepetářová, Blanka (UOCHB-X) RID, ORCID
Hocek, Michal (UOCHB-X) RID, ORCIDNumber of authors 4 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 75, č. 2 (2010), s. 442-449Number of pages 8 s. Language eng - English Country US - United States Keywords C-nucleosides ; pyridines ; cross-coupling ; amination Subject RIV CC - Organic Chemistry R&D Projects LC512 GA MŠMT - Ministry of Education, Youth and Sports (MEYS) IAA400550902 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR) CEZ AV0Z40550506 - UOCHB-X (2005-2011) UT WOS 000273400300020 DOI 10.1021/jo902313g Annotation An efficient and practical methodology of preparation of 6-substituted pyridin-2-yl C-ribonucleosides was developed. The key intermediate, TBS-protected 6-bromopyridine C-ribonucleoside, was prepared by the addition of 2-lithio-6-bromopyridine to TBS-protected ribonolactone followed by acetylation and reduction with Et3SiH and BF3.Et2O. It was then subjected to cross-coupling reactions, aminations and aminocarbonylations followed by deprotections to give a series title 1beta-(6-alkyl-, 6-aryl-, 6-amino- and 6-carbamoylpyridin-2-yl)-C-ribonucleosides. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2011
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