N→N Alkyl and Glycosyl Migrations of Purines and Pyrimidines. IV. trans-Glycosylation from Pyrimidines to Purines. (A Novel Synthetic Method of Purine Nucleosides and Nucleotides)

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Application of N3→N9(N7) migration reaction of purine derivatives led to a novel synthetic procedure of purine nucleosides and nucleotides. Direct transfer of ribosyl moieties of acylated pyrimidine nucleosides, nucleotides and trimethylsilylated nucleotides to purine bases was successfully carried out in the pressence of catalyst. Adenosine, N6, N6-dimethyladenosine, inosine, guanosine, 7-D-ribofuranosylguanine, 7-D-ribofuranosyl theophylline, adenosine 5'-phosphate, 7-D-ribofuranosyl theophylline 5'-phosphate and other glycosyl derivatives were obtained by transglycosylation reaction. Preparation of purine nucleosides and nucleotides by this transglycosylation reaction must be a valuable method for utilization of useless pyrimidine nucleotides which are produced during degradation of RNA together with useful purine nucleotides as seasoning.

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