Preparation of O'-METHYL derivatives of 9-beta-D-xylofuranosyladenine.
Treatment of the therapeutically important 9-beta-D-xylofuranosyladine in strongly alkaline medium with dimethyl sulphate led principally to etherification of sugar hydroxyls and, to a minor extent, to formation of products with a methylated exocyclic amino group. The various O'-methyl derivatives of xylofuranosyladenine were fractionated on a strongly basic ion exchange column, and isolated in pure form. Also isolated was 9-beta-D-xylofuranosyl-N6-methyladenine and its 2'-O-methyl derivative. The products were identified from their 1H NMR spectra, for which extensive data are tabulated. The susceptibilities of the various derivatives to calf intestinal adenosine deaminase were examined in relation to those of other adenine nucleosides; in particular, 5'-O-methylation led to total loss of substrate properties for the riboside, arabinoside and xyloside of adenine.
D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000818:Animals; D002417:Cattle; D008722:Methods; D008745:Methylation
D000241:Adenosine