81308-58-9Relevant academic research and scientific papers
SYNTHESIS AND GLYCOSIDIC BOND CLEAVAGE OF 7-METHYL- AND 7-ETHYL-ADENOSINES: AN ALTERNATIVE SYNTHESIS OF 7-ALKYLADENINES
Fujii, Tozo,Saito, Tohru
, p. 117 - 123 (2007/10/02)
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 deg C for 40 min, VIIa (X = ClO4) and VIIb (X = ClO4) produced 7-methyladenine (VIIIa) and 7-ethyladenine (VIIIb) in 84percent and 55percent yields.In 0.1 N aqueous HCl at 25 deg C, VIIa (X = ClO4) and VIIb (X = ClO4) were hydrolyzed in similar manners at rates of 2.22E-3 min-1 and 1.69E-3 min-1, respectively.Comparison of these rate conctants 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).
