메뉴 건너뛰기




Volumn 61, Issue 13, 1996, Pages 4405-4411

Efficient and β-stereoselective synthesis of 4(5)-(β-D-ribofuranosyl)- and 4(5)-(2-deoxyribofuranosyl)imidazoles

Author keywords

[No Author keywords available]

Indexed keywords

C NUCLEOSIDE; IMIDAZOLE DERIVATIVE;

EID: 0030018446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo952136z     Document Type: Article
Times cited : (48)

References (49)
  • 2
    • 0003586747 scopus 로고
    • Wiley-Interscience: New York
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1979) J. Nucleosides as Biological Probes
    • Suhadolnik, R.1
  • 3
    • 0022177192 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1985) Prog. Med. Chem. , vol.22 , pp. 1
    • Hacksell, U.1    Daves, G.D.2
  • 4
    • 84998446077 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1980) Yuki Gosei Kagaku Kyokai Shi , vol.38 , pp. 862
    • Sato, T.1    Noyori, R.2
  • 5
    • 85007934594 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1980) Yuki Gosei Kagaku Kyokai Shi , vol.38 , pp. 947
    • Sato, T.1    Noyori, R.2
  • 6
    • 85004388092 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1987) Yuki Gosei Kagaku Kyokai Shi , vol.45 , pp. 212
    • Watanabe, K.A.1
  • 7
    • 85007734527 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1989) Yuki Gosei Kagaku Kyokai Shi , vol.47 , pp. 707
    • Katagiri, N.1
  • 8
    • 0026714006 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1992) Tetrahedron , vol.48 , pp. 8545
    • Postema, M.H.D.1
  • 9
    • 0028323434 scopus 로고
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1994) Synthesis , pp. 1
    • Jaramillo, C.1    Knapp, S.2
  • 10
    • 0000457348 scopus 로고
    • The Chemistry of C-Nucleosides
    • Townsend, L. B., Ed.; Plenum Press: New York
    • For recent reviews on the chemisty, biochemistry, and synthesis of C-nucleoside analogues, see: (a) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979. (b) Hacksell, U.; Daves, G. D. Prog. Med. Chem. 1985, 22, 1. (c) Sato, T.; Noyori, R. Yuki Gosei Kagaku Kyokai Shi 1980, 38, 862. (d) Sato, T.; Noyori, R. Ibid. 1980, 38, 947. (e) Watanabe, K. A. Ibid. 1987, 45, 212. (f) Katagiri, N. Ibid. 1989, 47, 707. (g) Postema, M. H. D. Tetrahedron 1992, 48, 8545. (h) Jaramillo, C.; Knapp, S. Synthesis 1994, 1. (i) Watanabe, K. A. The Chemistry of C-Nucleosides. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1994; Vol. 3, pp 421-535.
    • (1994) Chemistry of Nucleosides and Nucleotides , vol.3 , pp. 421-535
    • Watanabe, K.A.1
  • 16
    • 0019861787 scopus 로고
    • 3 antagonists: (h) Rosen, T.; Nagel, A. A.; Rizzi, J. P. Synlett 1991, 213 and references cited therein.
    • (1981) J. Med. Chem. , vol.24 , pp. 913
    • Ganellin, R.1
  • 17
    • 0025191897 scopus 로고
    • 3 antagonists: (h) Rosen, T.; Nagel, A. A.; Rizzi, J. P. Synlett 1991, 213 and references cited therein.
    • (1990) J. Med. Chem. , vol.33 , pp. 4
    • Timmerman, H.1
  • 18
    • 15844393565 scopus 로고
    • and references cited therein
    • 3 antagonists: (h) Rosen, T.; Nagel, A. A.; Rizzi, J. P. Synlett 1991, 213 and references cited therein.
    • (1991) Synlett , pp. 213
    • Rosen, T.1    Nagel, A.A.2    Rizzi, J.P.3
  • 27
    • 33947476003 scopus 로고
    • Barker, R.; Fletcher, H. G., Jr. J. Org. Chem. 1961, 26, 4605. We obtained 5 in an improved yield (68%) from D-ribose by the Barker procedure.
    • (1961) J. Org. Chem. , vol.26 , pp. 4605
    • Barker, R.1    Fletcher Jr., H.G.2
  • 33
    • 15844409466 scopus 로고    scopus 로고
    • note
    • 1. More details on the crystal structure analysis (refcode: ZAPSUE) were submitted to the Cambridge Crystallographic Data Centre. The details can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
  • 38
    • 15844395273 scopus 로고    scopus 로고
    • note
    • 1′-2′ and NOE values of 11R and 11S did not show significant differences at 24°C.
  • 44
    • 15844374856 scopus 로고    scopus 로고
    • note
    • Reference 10b and references cited therein.
  • 48
    • 15844376379 scopus 로고    scopus 로고
    • note
    • HIV in MT-4 cells and type A Influenza virus in MDBK cells.
  • 49
    • 15844382010 scopus 로고    scopus 로고
    • note
    • CCD-19 Lu, CCRF-CEM, p388, p388/ADM, B16, Lewis, Lu-65, Lu-99, A549, RERF-LC-AI, and HT-29 cell lines.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.