Original title: Modular synthesis of 5-substituted thiophene and furan C-nucleosides and their analogues
Authors: Bárta, Jan ; Hocek, Michal
Document type: Papers
Conference/Event: Chemistry of Nucleic Acid Components /15./, Český Krumlov (CZ), 2011-06-05 / 2011-06-10
Year: 2011
Language: eng
Abstract: A new modular and efficient methodology for the preparation of 5-substituted thiophen-2-yl and 5-substituted furan-2-yl C-nucleosides was developed. A Friedel–Crafts-type of C-glycosidation of 2-bromothiophene or 2-bromofuran with bis-toluoyl protected methyl- 2′-deoxyribofuranoside in presence of Lewis acid gave the desired bis-toluoyl protected 5-bromothiophne and 5-bromofuran C-nucleosides in good yields. They were used as key intermediates for Stille or Suzuki coupling whith (hetero)arylstannanes or boronic acids to afford a series of 5-(hetero)aryl thiophene and 5-(heteroaryl)furan C-nucleosides.
Keywords: C-nucleosides; furan; thiophene
Project no.: CEZ:AV0Z40550506 (CEP), LC512 (CEP), IAA400550902 (CEP)
Funding provider: GA MŠk, GA AV ČR
Host item entry: Chemistry of Nucleic Acid Components. 15th Symposium, ISBN 978-80-86241-37-1

Institution: Institute of Organic Chemistry and Biochemistry AS ČR (web)
Document availability information: Fulltext is available at the institute of the Academy of Sciences.
Original record: http://hdl.handle.net/11104/0198837

Permalink: http://www.nusl.cz/ntk/nusl-55833


The record appears in these collections:
Research > Institutes ASCR > Institute of Organic Chemistry and Biochemistry
Conference materials > Papers