Regioselective modification of the sugar moiety in pyrimidine nucleosides via a 4′,5′-dehydro-2′,3′-anhydrouridine intermediate

Abstract

3′-Substituted pyrimidine nucleoside derivatives are obtained in moderate to high yields by the reactionof 1-(2′,3′-anhydro-5′-deoxy-4′,5′-didehydro-α-L-erythro-pentofuranosyl)uracil with nucleophiles without the formation of the corresponding 2′-adduct.

References

1. C. Perigaud, G. Gosselin and J.-L. Imbach, Nucleosides Nucleotides, 1992, 11, 903; L. R. Townsend, Chemistry of Nucleosides and Nucleotides, Plenum, New York, 1988; A. Matsuda, J. Synth. Org. Chem. Jpn., 1990, 48, 907; H. Maag, R. M. Rydzewski, M. J. McRoberts, D. Crawford-Ruth, J. P. H. Verheyden and E. J. Prisbe, J. Med. Chem., 1992, 35, 1440; M.-J. Camarasa, M.-J. Perez-Perez, A. San-Felix, J. Balzarini and E. De Clercq, J. Med. Chem., 1992, 35, 2721; M.-J. Perez-Perez, A. San-Felix, J. Balzarini, E. De Clercq and M.-J. Camarasa, J. Med. Chem., 1992, 35, 2988.
2. T. L. Ruth, Oligonucleotides and Their Analogues, IRL Press, London, 1991; B. Giese, P. Imwinkelried and M. Petretta, Synlett, 1994, 1003 and references therein.
3. (a) J. F. Cordington, R. Fecher and J. J. Fox, J. Am. Chem. Soc., 1960, 82, 2794; (b) N. C. Chang, J. H. Burchanel, R. Fecher, R. Duschinsky and J. J. Fox, J. Am. Chem. Soc., 1961, 83, 4060; (c) J. F. Cordington, R. Fecher and J. J. Fox, J. Org. Chem., 1962, 27, 163.
4. K. Minamoto, Y. Yamano, Y. Matsuoka, K. Watanabe, T. Hirata and S. Eguchi, Nucleosides Nucleotides, 1992, 11, 457; J. P. Horwits, J. Chua, M. A. D. Rooge, M. Noel and I. L. Klundt, J. Org. Chem., 1966, 31, 205; T. Sasaki, K. Minamoto and K. Hattori, Tetrahedron, 1974, 30, 2689; D. H. Hollenberg, K. A. Watanabe and J. J. Fox, J. Med. Chem., 1977, 20, 113; G. Kowollik and P. Z. Langen, Z. Chem., 1975, 15, 147; P. Herdewijin, A. Van Aerschot and L. Kerremans, Nucleosides Nucleotides, 1989, 8, 65; H. M. Misra, W. P. Gati, E. E. Kraus and L. I. Wiebe, J. Heterocycl. Chem., 1984, 21, 773; J.-T. Haung, L.-C. Chen, L. Wang, M.-H. Kim, J. A. Warshaw, D. Armstrong, Q.-Y. Zhu, T.-C. Chou, K. A. Watanabe and J. J. Fox, J. Med. Chem., 1991, 34, 1640; U. Reichman, D. H. Hollenberg, C. K. Chu, K. A. Watanabe and J. J. Fox, J. Org. Chem., 1976, 41, 2042; C. F. Hunnel and R. P. Carty, Nucleosides Nucleotides, 1983, 2, 249; M. E. Perlman and K. A. Watanabe, Nucleosides Nucleotides, 1989, 8, 145; D. Habich and W. Barth, Synthesis, 1988, 943; A. Mate, J. B. Hobbs, D. C. Scopes and R. F. Newton, Tetrahedron Lett., 1985, 26, 97; M. Ashwell, A. S. Jones and R. T. Walker, Nucleic Acids Res., 1987, 15, 2157; T. R. Webb, H. Mitsuya and S. Broder, J. Med. Chem., 1988, 31, 1475; M. J. Bamford, P. L. Coe and R. T. Walker, J. Med. Chem., 1990, 33, 2494; K. Hamaguchi, H. Tanaka, H. Maeda, Y. Itoh, S. Saito and T. Miyasaka, J. Org. Chem., 1991, 56, 5401; P. Wigerinck, A. V. Aerschot, G. Janssen, P. Claes, J. Balzarini, E. De Clercq and P. Herdewijin, J. Med. Chem., 1990, 33, 868; X. Ariza, J. Garces and J. Vilarrasa, Tetrahedron Lett., 1992, 33, 4069; I. L. Doerr, J. F. Cordington and J. J. Fox, J. Org. Chem., 1965, 30, 467.
5. V. Dalla and P. Pale, Tetrahedron Lett., 1996, 37, 2781.
6. J. A. Marshall, Chem. Rev., 1989, 89, 1503.