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Original Articles

Synthesis of Chiral 1′,2′-SECO-Nucleosides OF Guanine AND Uracil

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Pages 201-211 | Received 05 Apr 1988, Published online: 24 Oct 2006

References

  • Schaeffer , H. J. , Beauchamp , L. , de Miranda , P. , Elion , G. , Bauer , D. G. and Collins , P. 1978 . Nature, (London) , 272 : 583
  • Chu , C. K. and Cutler , S. J. 1986 . J. Heterocycl. Chem. , 23 : 289 For a recent review see
  • Schaeffer , H. J. 1983 . Nucleosides, Nucleotides and Their Biological Applications , Edited by: Rideout , J. L. , Henry , D. W. and Beacham , L. M. 1 – 17 . New York : Academic Press .
  • Martin , J. C. , Dvorak , C. A. , Smee , D. F. , Matthews , T. R. and Verheyden , J. P. H. 1983 . J. Med. Chem. , 26 : 759 and references cited therein
  • Martin , J. C. , McGee , D. P. C. , Jeffrey , G. A. , Hobbs , D. W. , Smee , D. F. , Matthews , T. R. and Verheyden , J. P. 1986 . J. Med. Chem. , 29 : 1384
  • Ashton , W. T. , Canning , L. F. , Reynolds , G. F. , Tolman , R. L. , Karkas , J. D. , Liou , R. , Davies , M. E. M. , DeWitt , C. M. , Perry , H. C. and Field , A. K. 1985 . J. Med. Chem. , 28 : 926
  • De Clercq , E. and Holy , A. 1979 . J. Med. Chem. , 22 : 510
  • De Clercq , E. , Holy , A. , Rosenberg , I. , Sakuma , T. , Balzarini , J. and Maudgal , P. C. 1986 . Nature (London) , 323 : 464 (b) A. Holy and I. Rosenberg, Collect. Czech. Chem. Commun., 52, 2775 (1987). (c) R. R. Webb II and J. C. Martin, Tetrahedron Lett., 28, 4963 (1987).
  • MacCoss , M. , Tolman , R. L. , Ashton , W. T. , Wagner , A. F. , Hannah , J. , Field , A. K. , Karkas , J. D. and Germershausen , J. I. 1986 . Chemica Scripta , 26 : 113 (b) M. MacCoss, A. Chen, and R. L. Tolman, Tetrahedron Lett., 26, 1815 (1985). (c) M. MacCoss, A. Chen, and R. L. Tolman, Tetrahedron Lett., 26, 4287 (1985).
  • 9-(1,3,4-Trihydroxy-2-butoxymethyl)guanine, was described by H. J. Schaeffer, ref. 3, but neither the experimental details nor the stereochemistry were given.
  • Abushanab , E. , Vemishetti , P. , Leiby , R. W. , Singh , H. K. , Mikkilineni , A. B. , Wu , D. C.-J. , Saibaba , R. and Panzica , R. P. 1988 . J. Org. Chem. , in press.
  • Vemishetti , P. , Leiby , R. W. , Abushanab , E. and Panzica , R. P. 1988 . J. Heterocyclic Chem. , in press.
  • Ogilvie , K. K. , Cheriyan , U. O. , Radatus , B. K. , Smith , K. O. , Galloway , K. S. and Kennell , W. L. 1982 . Can. J. Chem. , 60 : 3005
  • If after 23 h the reaction was worked up, 9-[(1,3S,4-tribenzyloxy-2R-butoxy)methyl]guanine9c, was the product. This material was crystallized from absolute ethanol {mp 168–170°C; [α]D 25, = −3.56 (c = 0.90, MeOH)} and was identical (tlc and 1H NMR) to an authentic sample provided by Drs. M. MacCoss and R. L. Tolman, (Merck).
  • Ogilvie , K. K. and Hanna , H. R. 1984 . Can. J. Chem. , 62 : 2702
  • Kjellberg , J. and Johansson , N. G. 1986 . Tetrahedron , 42 : 6541

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