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The ring opening of cyclopentene oxides by pyrimidines and purines as a pathway to carbocyclic nucleoside analogues

Ringöffnung von Cyclopentenoxiden mit Pyrimidinen und Purinen als Syntheseweg zu carbocyclischen Nucleosidanalogen

  • Organische Chemie Und Biochemie
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Summary

Various carbocyclic nucleosides withxylo-configuration have been synthesized using ring opening of 5-O-acetyl-1,2-anhydro-3-O-benzylcarba-α-DL-xylo-pentofuranose (6) by thymine, uracil, 4-N-benzoylcytosine, adenine, 6-N-benzoyladenine, and 2-amino-6-chloropurine in alkaline medium. For this purpose, the use of triethylaluminum is introduced into carbanucleoside chemistry. The new method proved to be superior over the application of sodium hydride and potassium or caesium carbonate.

Zusammenfassung

Ringöffnung von 5-O-Acetyl-1,2-anhydro-3-O-benzylcarba-α-DL-xylo-pentofuranose (6) mit Thymin, Uracil, 4-N-Benzoylcytosin, Adenin, 6-N-Benzoyladenin und 2-Amino-6-chlorpurin in alkalischem Medium ergab die entsprechendenxylo-konfigurierten carbocyclischen Nucleoside. Als Hilfsbase wurde Triethylaluminium verwendet, was deutliche Vorteile gegenüber der Verwendung von Natriumhydrid und Kalium- oder Cäsiumcarbonat bezüglich Produktreinheit und Ausbeute bietet.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Technical University Graz, A-8010, Graz, Austria

    H. Kapeller, H. Baumgartner, C. Marschner, R. Pucher & H. Griengl

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  1. H. Kapeller
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  2. H. Baumgartner
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  3. C. Marschner
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  4. R. Pucher
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  5. H. Griengl
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Kapeller, H., Baumgartner, H., Marschner, C. et al. The ring opening of cyclopentene oxides by pyrimidines and purines as a pathway to carbocyclic nucleoside analogues. Monatsh Chem 128, 953–960 (1997). https://doi.org/10.1007/BF00807105

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  • DOI: https://doi.org/10.1007/BF00807105

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