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Communication | Special issue | Vol 17, No. 1, 1982, pp.117-123
Published online, 1st January, 1970
DOI: 10.3987/S-1982-01-0117
Synthesis and Glycosidic Bond Cleavage of 7-Methyl- and 7-Ethyladenosines: An Alternative Synthesis of 7-Alkyladenines

Tozo Fujii* and Tohru Saito

*Faculty of Pharmaceutical Scicences, Kanazawa University, 13-1 Takara-machi, Kanazawa 920-0934, Japan


7-Methyladenosine perchlorate (VIIa: X = ClO4) was prepared in pure and crystalline form from N6-methoxyadenosine (I) by methylation with MeI at the 7-position followed by catalytic hydrogenolysis of the N6-methoxy group. 7-Ethyladenosine perchlorate (VIIb: X = ClO4) was also synthesized from N6-benzyloxyadenosine (II) in an analogous manner. On treatment with H2O at 98-100°C for 40 min, VIIa (X = ClO4) and VIIb (X = ClO4) produced 7-methyladenine (VIIIa) and 7-ethyladenine (VIIIb) in 84% and 55% yields. In 0.1 N aqueous HCl at 25°C, VIIa (X = ClO4) and VIIb (X = ClO4) were hydrolyzed in similar manners at rates of 2.22 ¥ 10-3 min-1 and 1.69 ¥ 10-3 min-1, respectively. Comparison of these rate constants with those of other three N-methyladenosine isomers X, XI, and XII has revealed that the relative ease of the hydrolysis of the glycosidic bond is in the order of 3- (XI) > 7- (VIIa) >> N6- (X) > 1-methyladenosine (XII).