Synthesis of 2′-β-C-methyl toyocamycin and sangivamycin analogues as potential HCV inhibitors

Coupling reaction of 2-β-C-methyl-1,2,3,4-tetra-O-benzoyl-d-ribofuranose with 4-amino-6-bromo-5-cyanopyrrolo[2,3-d]pyrimidine, followed by debromination and debenzoylation, gave the 2′-β-C-methyl toyocamycin in high yield. Based on this result, a series of 2′-β-C-methyl-4-substituted toyocamycin and sangivamycin analogues were synthesized for biological screening as potential inhibitors of HCV RNA replication.