Synthesis of 6,5'-cyclo-5'-deoxyuridines by radical cyclization (nucleosides and nucleotides. L)

Article abstract of DOI:10.1248/cpb.32.3410

6,5'-Cyclo-5'-deoxyuridine, a fixed anti form of uridine, was synthetized by a radical cyclization of 5'-bromo(or iodo)-5'-deoxy-2',3'-O-isopropylidene-5-chloro(or bromo)-uridine and tri-n-butyltin hydride followed by dehydrohalogenation and deacetonation. The 5-bromo and 4-thio derivatives of the cyclouridine were also prepared and were converted to the 2',3'-cyclic phosphates. These nucleotides were hydrolyzed by pancreatic ribonuclease. The result showed that the enzyme recognizes the pyrimidine nucleotides in the anti form. 6,5'-Cyclo-5'-deoxycytidine was also synthesized by two routes.

Full text of DOI:10.1248/cpb.32.3410

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