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Synthesis 1994; 1994(12): 1476-1484
DOI: 10.1055/s-1994-25717
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A Novel Route to Pyrimidine Nucleosides via Intramolecular Couplings of Bases with 2′-Deoxyribosides: Quick and Stereospecific...but with a 'Twist'

Bruce H. Lipshutz* , Hiroyuki Hayakawa, Kaneyoshi Kato, Richard F. Lowe, Kirk L. Stevens
  • *Department of Chemistry, University of California, Santa Barbara, CA, USA 93106-9510
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Publikationsdatum:
25. April 2002 (online)

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Coupling of a pyrimidine base (e.g., thymine) with the C-5′ hydroxyl group of a 2′-deoxyriboside via bromoetherification leads to intermediates which can be converted to cyclonucleosides under the influence of Lewis acids. Ring opening by β-elimination affords nucleosides which are stereopure at the required anomeric position.