Cyclopentane-nucleobase coupling in the synthesis of carbocyclic L-nucleosides: is a SN2-reaction an alternative to the Mitsunobu-reaction?
Several carbocyclic L-nucleosides have been synthesized by coupling a cyclopentane-system with heterocycles according to a modified Mitsunobu-protocol. This reaction gave two regioisomers, the N1-alkylated product and an unwanted O(2)-product. A simple S(N)2-reaction has been investigated as an alternative for such couplings.
Department of Chemistry, Organic Chemistry, Faculty of Science, University of Hamburg, Hamburg, Germany.
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D000478:Alkylation; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry; D003517:Cyclopentanes / Q000737:chemistry; D015195:Drug Design; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
D000998:Antiviral Agents; D003517:Cyclopentanes; D009705:Nucleosides; D011741:Pyrimidine Nucleosides