Bioorganic & medicinal chemistry

Synthesis of functionalized biphenyl-C-nucleosides and their incorporation into oligodeoxynucleotides

A Zahn, CJ Leumann

Index: Zahn, Alain; Leumann, Christian J. Bioorganic and Medicinal Chemistry, 2006 , vol. 14, # 18 p. 6174 - 6188

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Citation Number: 21

Abstract

We describe the synthesis of eight novel C-nucleosides in which the nucleobases are replaced by biphenyl residues that carry one or two electron donor (–OCH3,–NH2) or acceptor (–NO2) functional groups in the distal ring. These C-nucleosides were synthesized convergently and in high yields from a common bromophenyl-C-nucleoside precursor via Suzuki coupling with the respective boronic acids or esters. These nucleosides were ...