A new efficient method for stereoselective synthesis of 2-deoxy-C-ribofuranosides

Chemistry Letters

Volumn , Issue 8, 1996, Pages 629-630

  Mukaiyama, Teruaki ^a   Uchiro, Hiromi ^a   Hirano, Noriyuki ^a   Ishikawa, Tatsuya ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030506198     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.629     Document Type: Article

References (13)

1. F. F. Davis and F. W. Allen, J. Biol. Chem., 227, 907(1957); W. E. Cohn, Fed. Proc., 16, 166(1957).
2. F. F. Davis and F. W. Allen, J. Biol. Chem., 227, 907(1957); W. E. Cohn, Fed. Proc., 16, 166(1957).
3. General review of C-nucleosides or C-nucleoside antibiotics: K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleosides and Nucleotides," ed by L. B. Townsend, Plenum Press, New York (1994), vol. 3, p. 421; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 44, 243(1983); K. A. Watanabe, J. Synth. Org. Chem. Jpn., 45, 212(1987).
4. General review of C-nucleosides or C-nucleoside antibiotics: K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleosides and Nucleotides," ed by L. B. Townsend, Plenum Press, New York (1994), vol. 3, p. 421; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 44, 243(1983); K. A. Watanabe, J. Synth. Org. Chem. Jpn., 45, 212(1987).
5. General review of C-nucleosides or C-nucleoside antibiotics: K. A. Watanabe, "The Chemistry of C-Nucleosides," in "Chemistry of Nucleosides and Nucleotides," ed by L. B. Townsend, Plenum Press, New York (1994), vol. 3, p. 421; J. G. Buchanan, Prog. Chem. Org. Nat. Prod., 44, 243(1983); K. A. Watanabe, J. Synth. Org. Chem. Jpn., 45, 212(1987).
6. Review of 2'-deoxyribo-C-nucleoside synthesis: L. J. S. Knutsen, Nucleoside Nucleotide, 11, 961(1992).
7. T. Mukaiyama, N. Hirano, M. Nishida, and H. Uchiro, Chem. Lett., 1996, 99.
8. Other examples of stereoselective N-or C-Glycosylation of 2-deoxyribose derivative utilizing the remote participation by 3-O-protecting group are as follows: A. J. Hubbard, A. S. Jones, R. T. Walker, Nucleic Acids Res., 12, 6827(1984); S. Yasumoto, H. Matsumoto, Y Tada, K. Kobayashi, and K. Noguchi, Jpn. Pat., 62, 187483(1987); T. Okauchi, H. Kubota, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845(1989); H. Togo, S. Ishigami, and M. Yokoyama, Chem. Lett., 1992, 1673; R. J. Young, S. Shaw-Ponter, G. W. Hardy, and G. Mills, Tetrahedron Lett., 35, 8687(1994).
9. Other examples of stereoselective N-or C-Glycosylation of 2-deoxyribose derivative utilizing the remote participation by 3-O-protecting group are as follows: A. J. Hubbard, A. S. Jones, R. T. Walker, Nucleic Acids Res., 12, 6827(1984); S. Yasumoto, H. Matsumoto, Y Tada, K. Kobayashi, and K. Noguchi, Jpn. Pat., 62, 187483(1987); T. Okauchi, H. Kubota, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845(1989); H. Togo, S. Ishigami, and M. Yokoyama, Chem. Lett., 1992, 1673; R. J. Young, S. Shaw-Ponter, G. W. Hardy, and G. Mills, Tetrahedron Lett., 35, 8687(1994).
10. Other examples of stereoselective N-or C-Glycosylation of 2-deoxyribose derivative utilizing the remote participation by 3-O-protecting group are as follows: A. J. Hubbard, A. S. Jones, R. T. Walker, Nucleic Acids Res., 12, 6827(1984); S. Yasumoto, H. Matsumoto, Y Tada, K. Kobayashi, and K. Noguchi, Jpn. Pat., 62, 187483(1987); T. Okauchi, H. Kubota, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845(1989); H. Togo, S. Ishigami, and M. Yokoyama, Chem. Lett., 1992, 1673; R. J. Young, S. Shaw-Ponter, G. W. Hardy, and G. Mills, Tetrahedron Lett., 35, 8687(1994).
11. Other examples of stereoselective N-or C-Glycosylation of 2-deoxyribose derivative utilizing the remote participation by 3-O-protecting group are as follows: A. J. Hubbard, A. S. Jones, R. T. Walker, Nucleic Acids Res., 12, 6827(1984); S. Yasumoto, H. Matsumoto, Y Tada, K. Kobayashi, and K. Noguchi, Jpn. Pat., 62, 187483(1987); T. Okauchi, H. Kubota, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845(1989); H. Togo, S. Ishigami, and M. Yokoyama, Chem. Lett., 1992, 1673; R. J. Young, S. Shaw-Ponter, G. W. Hardy, and G. Mills, Tetrahedron Lett., 35, 8687(1994).
12. Other examples of stereoselective N-or C-Glycosylation of 2-deoxyribose derivative utilizing the remote participation by 3-O-protecting group are as follows: A. J. Hubbard, A. S. Jones, R. T. Walker, Nucleic Acids Res., 12, 6827(1984); S. Yasumoto, H. Matsumoto, Y Tada, K. Kobayashi, and K. Noguchi, Jpn. Pat., 62, 187483(1987); T. Okauchi, H. Kubota, and K. Narasaka, Bull. Chem. Soc. Jpn., 62, 845(1989); H. Togo, S. Ishigami, and M. Yokoyama, Chem. Lett., 1992, 1673; R. J. Young, S. Shaw-Ponter, G. W. Hardy, and G. Mills, Tetrahedron Lett., 35, 8687(1994).
13. 4 and three equivalent of AgOTf in toluene.