Synthesis of cyclobutane nucleosides

Nucleosides Nucleotides Nucleic Acids. 2011 Jun;30(6):391-404. doi: 10.1080/15257770.2011.584513.

Abstract

2-(6-Chloropurinyl)-3-benzoyloxymethylcyclobutanone can be prepared by reaction of 6-chloropurine with 3-benzoyloxymethyl-2-bromocyclobutanone. The N-alkylation gave both N-9 and N-7 regioisomers. Both regioisomers upon hydride reduction followed by aminolysis gave the corresponding adenine nucleoside analogues. However, the N-7 series led to the hypoxanthine analogues as byproducts.

MeSH terms

  • Adenine / analogs & derivatives
  • Alkylation
  • Cyclobutanes / chemical synthesis
  • Cyclobutanes / chemistry*
  • Isomerism
  • Models, Molecular
  • Nucleosides / chemical synthesis
  • Nucleosides / chemistry*

Substances

  • Cyclobutanes
  • Nucleosides
  • Adenine