Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Nucleosides and Nucleotides. XIII. Synthesis of Thiopurine Nucleosides from Adenosine and Guanosine Derivatives by the Sulfhydrolysis
KAZUNOBU MIURATOHRU UEDA
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1975 Volume 23 Issue 9 Pages 2064-2069

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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.
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© The Pharmaceutical Society of Japan
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