Synthesis of Cyclobutane Nucleosides

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 nucleosi...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2011-06, Vol.30 (6), p.391-404
Main Authors: Ebead, Abdelaziz, Fournier, Rene, Lee-Ruff, Edward
Format: Article
Language:English
Subjects:
Adenine - analogs & derivatives
Alkylation
Carbocyclic nucleosides
cyclobutane nucleosides
Cyclobutanes - chemical synthesis
Cyclobutanes - chemistry
cyclobutanone
Isomerism
Models, Molecular
Nucleosides - chemical synthesis
Nucleosides - chemistry
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Summary: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.
ISSN:1525-7770
1532-2335
DOI:10.1080/15257770.2011.584513