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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
- 1.0342342 - ÚOCHB 2011 RIV US eng J - Journal Article
Štefko, Martin - Slavětínská, Lenka - Klepetářová, Blanka - Hocek, Michal
A General and Efficient Synthesis of Pyridin-2-yl C-Ribonucleosides Bearing Diverse Alkyl, Aryl, Amino and Carbamoyl Groups in Position 6.
Journal of Organic Chemistry. Roč. 75, č. 2 (2010), s. 442-449. ISSN 0022-3263. E-ISSN 1520-6904
R&D Projects: GA MŠMT LC512; GA AV ČR IAA400550902
Institutional research plan: CEZ:AV0Z40550506
Keywords : C-nucleosides * pyridines * cross-coupling * amination
Subject RIV: CC - Organic Chemistry
Impact factor: 4.002, year: 2010
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.
Permanent Link: http://hdl.handle.net/11104/0185098
Number of the records: 1