One-Flask Syntheses of 6-Thioguanosine and 2′-Deoxy-6-Thioguanosine

Pei Pei Kung, Roger A. Jones

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

We have previously reported that reaction of guanosine or 2′-deoxyguanosine with trifluoroacetic anhydride in pyridine gives a putative 6-pyridyl intermediate from which several 6-substituted derivatives may be obtained.1 We now report high-yield conversion of guanosine and 2′-deoxyguanosine to the corresponding 6-thio compounds in a two-step, one-flask reaction via this 6-pyridyl intermediate. Standard Raney nickel treatment, as reported for the ribonucleoside,2 then gives the 2-aminopurine nucleosides.

Original languageEnglish (US)
Pages (from-to)3919-3922
Number of pages4
JournalTetrahedron Letters
Volume32
Issue number32
DOIs
StatePublished - Aug 5 1991

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Keywords

  • 2-amino-9-(2-deoxy-β-D-erythro-pentofuranosyl)purine
  • 2′-deoxy-6-thioguanosine
  • 6-Thioguanosine

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