title: Synthesis of 2,6-disubstituted pyridin-3-yl C-2'-deoxyribonucleosides through chemoselective transformations of bromo-chloropyridine C-nucleosides.
abstract: 2-Bromo-6-chloro- and 6-bromo-2-chloropyridin-3-yl deoxyribonucleosides were prepared by the Heck coupling of bromo-chloro-iodopyridines with TBS-protected deoxyribose glycal. Some of their Pd-catalyzed cross-coupling reactions proceeded chemoselectively at the position of the bromine, whereas nucleophilic substitutions were unselective and gave mixtures of products. The mono-substituted intermediates were used for another coupling or nucleophilic substitution giving rise to a small library of title 2,6-disubstituted pyridine C-deoxyribonucleosides. The title nucleosides did not exert antiviral or cytostatic effects.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead & IOCB Research Center, Flemingovo nam. 2, CZ-16610 Prague 6, Czech Republic.
authors.forename: Tomáš
authors.initials: T
authors.lastname: Kubelka
authors.forename: Lenka
authors.initials: L
authors.lastname: Slavětínská
authors.forename: Václav
authors.initials: V
authors.lastname: Eigner
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D060326:Chemistry Techniques, Synthetic; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013379:Substrate Specificity
chemical_list: D003853:Deoxyribonucleosides; D011725:Pyridines; C023666:pyridine