Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Nucleosides and Nucleotides. X. Synthesis of 4-Thiouracil Nucleosides and Nucleotides by the Solvolysis of Cytidine and Its Phosphates with Hydrogen Sulfide
TOHRU UEDAKAZUNOBU MIURAMASAOKI IMAZAWAKEIKO ODAJIMA
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1974 Volume 22 Issue 10 Pages 2377-2382

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Abstract
Treatment of cytidine with liquid hydrogen sulfide-pyridine afforded 4-thiouridine in an excellent yield. Similar treatment of sodium cytidine 5'-phosphate, cytidine 5'-diphosphate (CDP), cytidine 5'-triphosphate (CTP), and CDP-choline afforded the respective 4-thiouridine phosphates. In the case of CDP and CTP the hydrolytic cleavage of pyrophosphate linkage was noticed. Several cytidine derivatives such as arabinofuranosylcytosine, 3-methylcytidine, and 2-thiocytidine also underwent sulfhydrolysis affording respective 4-thio derivatives. The present method seemed to be the most versatile procedure for the synthesis of-4 thiouracil nucleosides and nucleotides.
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© The Pharmaceutical Society of Japan
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