Pyrimidine S- and N-Cyclonucleosides. Synthesis of 6,2'(and 5')-S- and N-Cyclouridines (Nucleosides and Nucleotides. XXXII)

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The synthesis of S- and N-cyclouridines, which are "anti"-fixed cyclonucleosides, is described. Bromination of S^2,2'-cyclo-2-thiouridine afforded the 5-bromo derivative. Cleavage of the S^2,2'-cyclo linkage of the 5-bromo derivative with methoxide resulted in the formation of S^6,2'-cyclo-2-O-methyluridine by intramolecular conversion of the S^2,2'-linkage to an S^6,2'-linkage, and this was further converted to the corresponding S^6,2'-cyclo derivatives of uridine, isocytidine and 2-thouridine. Similarly, 2', 3'-O-isopropylidene-S^2,5'-cyclo-2-thiouridine was converted to the 2', 3'-O-isopropylidene-S^6,5'-cyclo derivatives of uridine, isocytidine, and 2-thiouridine. 6-Methylaminouridine was cyclized by treatment with diphenyl carbonate to N^6,2'-cyclo-6-methylaminouridine. Cyclization with triphenylphosphine and diethyl azodicarboxylate gave the N^6,5'-cyclo derivative of 6-methylaminouridine.
社団法人日本薬学会の論文
1980-03-25