Synthesis of novel L-series 2',3'-dideoxy-3'-hydroxy-methyl-nucleosides and a convenient method for the separation of nucleoside anomers

Nucleosides and Nucleotides

Volumn 16, Issue 1-2, 1997, Pages 193-213

  Gould, Jayne H M ^a   Mann, John ^a  

^a UNIVERSITY OF READING   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHROMATOGRAPHY; DRUG SYNTHESIS; HEPATITIS; NONHUMAN; NUCLEOTIDE METABOLISM; PROTEIN STRUCTURE; PROTEIN TARGETING; STRUCTURE ANALYSIS;

EID: 0031057883     PISSN: 07328311     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328319708002533     Document Type: Article

References (18)

1. Excellent recent reviews on the subject of anti-HIV chemotherapy include: De Clercq, E. J.Med. Chem.. 1995, 38, 2491; Bochme, R.E., Borthwick, A.D. and Wyatt, P.G. Ann.Rept.Med.Chem., 1995, 30, 139.
2. Excellent recent reviews on the subject of anti-HIV chemotherapy include: De Clercq, E. J.Med. Chem.. 1995, 38, 2491; Bochme, R.E., Borthwick, A.D. and Wyatt, P.G. Ann.Rept.Med.Chem., 1995, 30, 139.
3. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
4. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
5. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
6. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
7. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
8. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
9. Kvarnstrom, I., Svansson, L., Svensson, C. and Svensson, S.C.T. Nucleosides Nucleotides. 1992, 11, 1367; Van Draanen and Koszalka, G.W. Nucloesides Nucleotides, 1994, 13, 1679; Lin, T-S., Luo, M-Z., Liu, M-C., Pai, S.B., Dutschman, G.E., and Cheng, Y-C. J.Med.Chem. 1994, 37, 798; Gosselin, G., Mathe, C., Bergogne, M-C., Aubertin, A-M., Kim, A., Sommadossi, J-P., Schinazi, R., and Imbach, J-L. Nucleosides Nucleotides. 1995, 14, 611; Ma, T., Pai, S.B., Zhu, Y.L., Lin, J.S., Shanmuganathan, K., Du, J., Wang, C. Kim, H., Newton, M.G., Cheng, Y.C., and Chu, C.K. J.Med. Chem. 1996, 39, 2835; Lin, T-S., Luo, M-Z., Liu, M-C., Zhu, Y-L., Gullen, E., Dutschman, G.E. and Cheng, Y-C. J.Med.Chem. 1996, 39, 1757; Selwood, D.L., Carter, K., Young, R.J. and Jandu, K.S. Biorg. Med Chem.Lett. 1996, 6, 991.
10. Mann, J. and Weymouth-Wilson, A.C. J.Chem.Soc.Perkin Trans. 1. 1994, 3141.
11. Hubschwerlen, C., Specklin, J-L. and Higelin, J. Org.Synth., 1993, 72, 1.
12. Mann, J., Partlett, N.K. and Thomas, A. J.Chem.Res. 1987, S, 369.
13. Young, R.J., Shaw-Ponter, S., Hardy, G.W., and Mills, G. Tet.Lett. 1994, 35, 8687.
14. Sugimura, H., Sujino, K. and Osumi, I. Tet. Lett., 1992, 33, 2515.
15. Kohn, P. Lerner, L.M., Chan, A., Ginocchio, S.D. and Zitrin, C.A. Carb.Res., 1968, 7, 21.
16. Tse, A. and Mansour, T.S.. Tet.Lett., 1995, 36, 7807.
17. Himmelsbach, F., Schulz, B.S., Trichtinger, T., Charubala, R. and Pfleider, W. Tetrahedron, 1984, 40, 59.
18. Perrin, D.D. and Annarego, W.L.F. Purification of Laboratory Chemicals, Pergamon Press, 3rd. edition, Oxford, UK, 1988.