Nucleosides and Nucleotides. XIII. Synthesis of Thiopurine Nucleosides from Adenosine and Guanosine Derivatives by the Sulfhydrolysis

Abstract

Synthesis of thiopurine nucleosides (and nucleotides) by the application of aminothiono exchange reaction (sulfhydrolysis) was described. 1-Methyl-6-thioinosine and 2', 3'-O-isopropylidene-5'-deoxy-3, 5'-cyclo-2-thioxanthosine were obtained from 1-methyladenosine and cycloguanosine, respectively. Sulfhydrolysis of a 3, 5'-cycloadenosine gave a 5-amino-N⁵, 5'-cycloimidazole-4-thiocarboxamide riboside in high yield. Synthesis of 6-thioinosine and 6-thioxanthosine by sulfhydrolysis of N⁶-methoxyadenosine and crotonoside, respectively, was also performed.