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

Chemical Communications

Volumn , Issue 18, 1999, Pages 1827-1828

  Hirota, Kosaku ^a   Takasu, Hideki ^a   Tsuji, Yoshie ^a   Sajiki, Hironao ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

PYRIMIDINE NUCLEOSIDE DERIVATIVE; SUGAR;

ARTICLE;

EID: 0033592462     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905608d     Document Type: Article

References (33)

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13. 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.
14. 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.
15. 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.
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18. 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.
19. 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.
20. 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.
21. 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.
22. 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.
23. 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.
24. 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.
25. 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.
26. 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.
27. 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.
28. 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.
29. 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.
30. 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.
31. 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.
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