An expeditious and efficient procedure for the synthesis of unsaturated acyclonucleosides of Z configuration related to D4T.
Enantiopure 2,5-dihydrofuran derivatives were prepared from (S)-glycidol through a new reaction sequence involving epoxide opening with a vinylcuprate, selenium-induced cyclization to give exclusively the 5-endo product, and regioselective selenoxide elimination. Unsaturated acyclonucleosides of Z configuration were obtained in a straightforward manner by treating 2,5-dihydrofuran with iodotrimethylsilane in the presence of silylated purinic or pyrimidinic bases. This synthetic process involves opening of the dihydrofuran ring by trimethylsilyl iodide and substitution of iodine by the nucleic base in a single reaction step.
Bravo
Fernando
F
Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, Pza. Imperial Tarraco 1, 43005 Tarragona, Spain.
Viso
Antonio
A
Castillón
Sergio
S
D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D002625:Chemistry, Organic / Q000379:methods*; D002855:Chromatography, Thin Layer; D004852:Epoxy Compounds / Q000737:chemistry; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009705:Nucleosides / Q000138:chemical synthesis*; D020005:Propanols / Q000737:chemistry; D012643:Selenium / Q000737:chemistry; D012821:Silanes / Q000737:chemistry; D013237:Stereoisomerism; D013941:Thymine / Q000031:analogs & derivatives / Q000138:chemical synthesis
D004852:Epoxy Compounds; D007202:Indicators and Reagents; D009705:Nucleosides; D020005:Propanols; D012821:Silanes; D012643:Selenium; D000225:Adenine; D013941:Thymine; C004312:glycidol