Syntheses of N4,2',3',5'-Tetraacylcytidines from N4-Acylcytosines, via Condensation with Tetraacylribose and Transribosylation with Acylated Purine Nucleosides

Yoshihiro Sugiura, S. Yuichi Furuya, Yoshiyasu Furukawa

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

N4-Isobutyryl- and -(2-ethylhexanoyl)cytosines (la, b) were synthesized by acylation of cytosine. Y4,2',3',5'-Tetraacylcytidines (III) were synthesized by two methods involving stannic chloride catalysis. One involves condensation of N4-acylcytosines (I) and l-0-acetyl-2,3,5-tri-0-benzoyl-β-D-ribofuranose (II), and the other involves transribosylation between N4-acylcytosines and acyl-inosines or -guanosines (IVa—d). N4-Octanoyl-2',3',5'-triacetylcytidine (Illf) was converted into cytidine by deacylation in a good yield.

Original languageEnglish
Pages (from-to)3253-3256
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume36
Issue number9
DOIs
Publication statusPublished - 1988

Keywords

  • 2',3 ',5 ',-tetraacylcytidine
  • N4-acylcytosine N4
  • acylinosine
  • condensation acylribose
  • stannic chloride
  • synthesis acylguanosine
  • transribosylation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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