A facile synthesis of 6-aryl-5-cyano-1-(β-D-pyranosyl or β-D-furanosyl)-2-thiocytosines

Ibrahim M. Abdou, Lucjan Strekowski

Research output: Contribution to journalArticlepeer-review

27 Citations (Scopus)

Abstract

The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-α-D-pyranosyl bromide produces a mixture of N1-(β-D-pyranosyl)-2-thiouracil and its N1, S2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-peracetyl-β-D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the β-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to β-D-ribosyl nucleosides.

Original languageEnglish
Pages (from-to)8631-8636
Number of pages6
JournalTetrahedron
Volume56
Issue number44
DOIs
Publication statusPublished - Oct 27 2000
Externally publishedYes

Keywords

  • 1 -(β-D-furanosyl)-2-thiocytosines
  • 1-(β-D-pyranosyl)-2-thiocytosines
  • 6-aryl-5-cyano-2-thiouracils
  • Ammonolysis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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