Synthesis of 2′-O, 4′-C-alkylene-bridged ribonucleosides and their evaluation as inhibitors of HCV NS5B polymerase

…, M La Colla, BA Mayes, JF McCarville, S Moore…

Index: Chapron, Christopher; Glen, Rebecca; La Colla, Massimiliano; Mayes, Benjamin A.; McCarville, Joseph F.; Moore, Stephen; Moussa, Adel; Sarkar, Ruhul; Seifer, Maria; Serra, Ilaria; Stewart, Alistair Bioorganic and Medicinal Chemistry Letters, 2014 , vol. 24, # 12 p. 2699 - 2702

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Citation Number: 6

Abstract

Abstract The synthesis of 2′-O, 4′-C-methylene-bridged bicyclic guanine ribonucleosides bearing 2′-C-methyl or 5′-C-methyl modifications is described. Key to the successful installation of the methyl functionality in both cases was the use of a one-pot oxidation– Grignard procedure to avoid formation of the respective unreactive hydrates prior to alkylation. The 2′-C-methyl-and 5′-C-methyl-modified bicyclic guanosines were ...