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Modular Synthesis of 5-Substituted Furan-2-yl C-2'-Deoxyribonucleosides and Biaryl Covalent Base-pair Analogues
- 1.0350078 - ÚOCHB 2011 RIV DE eng J - Journal Article
Bárta, Jan - Slavětínská, Lenka - Klepetářová, Blanka - Hocek, Michal
Modular Synthesis of 5-Substituted Furan-2-yl C-2'-Deoxyribonucleosides and Biaryl Covalent Base-pair Analogues.
European Journal of Organic Chemistry. -, č. 28 (2010), s. 5432-5443. ISSN 1434-193X. E-ISSN 1099-0690
R&D Projects: GA MŠMT LC512; GA AV ČR IAA400550902
Institutional research plan: CEZ:AV0Z40550506
Keywords : C-nucleosides * furans * C-glycosidation * cross-coupling reactions
Subject RIV: CC - Organic Chemistry
Impact factor: 3.206, year: 2010
A modular and efficient synthesis of 5-(hetero)arylfuran C-2'-deoxyribonucleosides was developed. Friedel–Crafts C-glycosidation of 2-bromofuran with toluoyl-protected methyl 2'-deoxyribofuranoside in the presence of BF3·Et2O gave 5- bromofuran C-nucleosides, which were used as key intermediates for Stille or Suzuki coupling with (hetero)arylstannanes or boronic acids to afford a series of 5-(hetero)arylfuran C-nucleosides.
Permanent Link: http://hdl.handle.net/11104/0190171
Number of the records: 1