Purines. LXI. An attempted synthesis of 2'-deoxy-7-methyladenosine: Glycosidic hydrolyses of the N6-methoxy derivative and 2'-deoxy-N(x)- methyladenosines

Article abstract of DOI:10.1248/cpb.42.495

In an attempt to synthesize 2'-deoxy-7-methyladenosine (5b), 2'-deoxy- N⁶-methoxyadenosine (13b) was treated with MeI in AcNMe₂ at 0°C for 7h to give the 2'-deoxy-N⁶-methoxy-7-methyladenosine salt (14b), which was unstable and easily underwent glycosidic hydrolysis in H₂O at 16-18°C to form N⁶-methoxy-7-methyladenine (15). On account of such instability, hydrogenolysis of 14b in H₂O using hydrogen and Raney Ni catalyst failed to afford the desired nucleoside (5b). 2'-Deoxy-N⁶-methyladenosine (2b), 2'- deoxy-1-methyladenosine (3b), and 14b were found to undergo glycosidic hydrolysis in 0.1 N aqueous HCl at 25°C at rates of 7.92 x 10^-2 min^-1 (half-life 87.5 min), 5.02 x 10^-3min^-1 (half-life 138 min), and 2.31 x 10^-2 min^-1 (half-life 30.0 min), respectively, while the rate in the case of 5h was roughly estimated to be ca. 2 min^-1 (half-life 0.35 min).

Full text of DOI:10.1248/cpb.42.495

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