125072-30-2Relevant academic research and scientific papers
3-METHYLXANTHOSINE: SYNTHESIS AND ACIDIC HYDROLYSIS OF THE GLYCOSYL BOND
Itaya, Taisuke,Harada, Tsunehiro
, p. 1235 - 1238 (2007/10/02)
An improved synthesis of 3,9-dimethylxanthine (2a) was achieved via the reaction of 1-methyl-5-(methylamino)-imidazole-4-carboxamide (3a) with EtOCOCl in acetate buffer (pH 5) followed by treatment with aqueous NaOH.This method was successfully applied to the synthesis of 3-methylxanthosine (2b), whose N-glycosidic bond proved to be remarkably sensitive to acidic hydrolysis: 2b underwent hydrolysis at a rate more than 1000 times faster than that of xanthosine (10) in 1.0N aqueous HCl at 25 deg C.Keywords: 3-methylxanthosine synthesis; 3,9-disubstituted xanthine; imidazolylcarbamic acid ester; base-catalyzed cyclization; amide carbamate cyclization; N-glycosidic bond hydrolysis; carbamate cis-trans isomerism; NMR; kinetic study
