Dr RC Mishra

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Describe here are, two approaches for the synthesis of 2′-C-β-methyl-2′-deoxyguanosine 3 via 2′-radical deoxygenation. One approach starts from 1,3,5-tri-O-benzoyl-α-d-ribofuranose 6 and gives 3 in 11 steps with 9.7% overall yield. The second approach starts from guanosine and gives 3 in 8 steps with 23% overall yield.

2′-C-Branched nucleosides represent a class of nucleoside analogues that have potential utility as therapeutic agents and as probes to study RNA structure and function.1-11 For example, 2′-C-β-methyl and 2′-deoxy-2′-C-α/β-methyl ribonucleosides, including 2′-C-β-methylguanosine 1, have antitumor and antiviral activities as inhibitors for Hepatitis C viral RNA replication.1-9 Recently, we used 2′-C-β-methyl nucleosides and 2′-deoxy-2′-C-α/β-methyl nucleosides, including 2′-C-α-methyl-2′-deoxyguanosine 2, to study the packing density of the P4−P6 RNA domain and the mechanism of Group II intron catalysis.10, 11 We previously reported an efficient synthesis of 2′-C-β-methylguanosine 112 and 2′-C-α-methyl-2′-deoxyguanosine 2.13 Here we report the synthesis of 2′-C-β-methyl-2′-deoxyguanosine 3 Figure 1.

via Synthesis of 2′-C-β-Methyl-2′-deoxyguanosine – The Journal of Organic Chemistry ACS Publications.