Modular Synthesis of 5-Substituted Furan-2-yl C-2'-Deoxyribonucleosides and Biaryl Covalent Base-pair Analogues

0350078 - ÚOCHB 2011 RIV DE eng J - Článek v odborném periodiku
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
Grant CEP: GA MŠMT LC512; GA AV ČR IAA400550902
Výzkumný záměr: CEZ:AV0Z40550506
Klíčová slova: C-nucleosides * furans * C-glycosidation * cross-coupling reactions
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 3.206, rok: 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.
Trvalý link: http://hdl.handle.net/11104/0190171