Highly efficient synthesis of phosphorodithioates derived from 3′-thiothymidine by anhydro-ring opening of 2,3′-anhydro-5′-O-tritylthymidine with O,O-disubstituted phosphorodithioic acids

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Wojciech D[a with combining cedilla]bkowski, Izabela Tworowska, Wojciech D[a with combining cedilla]bkowski and Maria Michalska


Abstract

Thymidine 3′-S-phosphorodithioate 4 and dithymidine-3′-S-phosphorodithioate 7 derived from 3′-thiothymidine are synthesized in excellent yield under mild conditions by the nucleophilic ring opening of 2,3′-anhydrothymidine with phosphorodithioic acids.


References

  1. Oligonucleotides: Antisense Inhibitors of Gene Expression, ed. J. S. Cohen, Macmillan, London, 1989 Search PubMed.
  2. W. A. Picken, D. B. Olsen, F. Benseler and F. Eckstein, Science, 1991, 253, 314 CAS.
  3. A. Hampton, L. W. Brox and M. Bayer, Biochemistry, 1969, 8, 2303 CrossRef CAS; E. F. Rossomando, G. A. Cordis and G. D. Markham, Arch. Biochem. Biophys., 1983, 220, 71 CrossRef CAS.
  4. A. F. Cook, J. Am. Chem. Soc., 1970, 92, 190 CrossRef CAS.
  5. A. F. Cook, J. Am. Chem. Soc., 1970, 92, 190 CrossRef CAS; J. Nagyvary, S. Chladek and J. Roe, Biochem. Biophys. Res. Commun., 1970, 39, 878 CrossRef CAS; S. Chladek and J. Nagyvary, J. Am. Chem. Soc., 1972, 94, 2079 CrossRef CAS; J. Kresse, K. L. Nagpal, J. Nagyvary and J. T. Uchlic, Nucleic Acids Res., 1975, 2, 1 CAS.
  6. J. S. Vyle, X. Li and R. Cosstick, Tetrahedron Lett., 1992, 33, 3017 CrossRef CAS.
  7. R. Costick and J. S. Vyle, Nucleic Acids Res., 1990, 4, 829.
  8. X. Li, G. K. Scott, A. D. Baxter, R. J. Taylor, J. S. Vyle and R. Cosstick, J. Chem. Soc., Perkin. Trans. 1, 1994, 2123 RSC; L. B. Weinstein, D. J. Earnshaw, R. Cosstick and T. R. Cech, J. Am. Chem. Soc., 1996, 118, 10 341 CrossRef CAS; A. P. Higson, G. K. Scott, D. J. Earnshaw, A. D. Baxter, R. A. Taylor and R. Cosstick, Tetrahedron, 1996, 52, 1027 CrossRef CAS.
  9. X. Liu and C. B. Reese, Tetrahedron Lett., 1996, 37, 925 CrossRef CAS.
  10. A. Okruszek, M. Olesiak and W. J. Stec, Phosphorus Sulfur Silicon Relat. Elem., 1996, 111, 81.
  11. W. Kudelska and M. Michalska, Tetrahedron, 1986, 42, 629 CrossRef CAS and references cited therein M. Michalska, E. Brzezinska and P. Lipka, J. Am. Chem. Soc., 1991, 113, 7945 Search PubMed; H. Bielawska and M. Michalska, J. Carbohydr. Chem., 1991, 10, 107 CrossRef CAS; W. Kudelska and M. Michalska, Synthesis, 1995, 1539 CAS.
  12. W. D[a with combining cedilla]bkowski, J. Michalski and Q. Wang, Angew. Chem., Int. Ed. Engl., 1990, 29, 522 CrossRef; J. Heliński, W. D[a with combining cedilla]bkowski and J. Michalski, Nucleosides Nucleotides, 1993, 12, 597 CAS; W. D[a with combining cedilla]bkowski, I. Tworowska and R. Saiakhov, Tetrahedron Lett., 1995, 36, 9223 CrossRef CAS.
  13. S. Czernecki and J.-M. Valéry, Synthesis, 1991, 239 CrossRef CAS; G. V. Zaitseva, E. I. Kvasyuk, E. V. Vaaks, V. N. Barai, S. B. Bokut, A. I. Zinchenko and I. A. Mikhailopulo, Nucleosides Nucleotides, 1994, 13, 819 CAS; B.-Ch. Chen, S. L. Quinlan and J. G. Reid, Tetrahedron Lett., 1995, 36, 7961 CrossRef CAS.
  14. A. Okruszek, A. Sierzchala, M. Sochacki and W. J. Stec, Tetrahedron Lett., 1992, 33, 7585 CrossRef CAS; A. Okruszek, M. Olesiak, D. Krajewska and W. J. Stec, J. Org. Chem., 1997, 62, 2269 CrossRef CAS.
  15. B. Bennua-Skalmowski and H. Vorbrüggen, Nucleosides Nucleotides, 1996, 15, 739 CAS.
  16. J. L. Lefferts, K. C. Molloy, J. J. Zuckerman, I. Haiduc, C. Guta and D. Ruse, Inorg. Chem., 1980, 19, 1662 CrossRef CAS.