- Purines. LXI. An attempted synthesis of 2'-deoxy-7-methyladenosine: Glycosidic hydrolyses of the N6-methoxy derivative and 2'-deoxy-N(x)- methyladenosines
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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).
- Fujii,Saito,Iguchi
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p. 495 - 499
(2007/10/02)
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- The photosolvolysis of N-arylmethyladenines. Photoremovable N-arylmethyl protective groups for N-containing compounds
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N-arylmethyladenines are photolyzed in water, giving adenine and the corresponding arylmethanols.The reaction is not only observed when the arylmethyl group is a metasubstituted benzyl, but also with more complex substituents like imidazopyridin-6-ylmethyl.Meta-substituted arylmethyl groups are proposed as photoremovable N-protective groups in adenine chemistry.
- Er-Rhaimini, A.,Mohsinaly, N.,Mornet, R.
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p. 5757 - 5760
(2007/10/02)
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