Convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides†

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Yao-Hua Zhu and Pierre Vogel


Abstract

A convergent synthesis of (1→2)- and (1→4)-C-linked imino disaccharides was achieved by applying Nozaki–Kishi coupling of a hydroxyproline-derived carbaldehyde with isolevoglucosenone or levoglucosenone derived enol triflates.


References

  1. See, e.g.: A. Varki, Glycobiology, 1993, 3, 97 Search PubMed; P. R. Crocker and T. Feizi, Curr. Opin. Struct. Biol., 1996, 6, 679 CrossRef CAS; A. Varki, Proc. Natl. Acad. Sci. U.S.A., 1994, 91, 7390 CrossRef CAS; K. W. Moremen, R. B. Trimble and A. Herscovics, Glycobiology, 1994, 4, 113 CAS; B. Ganem, Acc. Chem. Res., 1996, 29, 340 CAS and references cited therein.
  2. R. Kornfeld and S. Kornfeld, Annu. Rev. Biochem., 1985, 54, 631 CrossRef CAS; A. Lai, P. Pang, S. Kalelkar, P. A. Romero, A. Herscovics and K. W. Moremen, Glycobiology, 1998, 8, 981 CrossRef and references cited therein.
  3. J. Marshall, J. Adv. Carbohydr. Chem. Biochem., 1974, 30, 257 Search PubMed; D. D. Schmidt, W. Frommer, B. Junge, L. Müller, W. Wingender, E. Truscheit and D. Schefer, Naturwissenschaften, 1977, 64, 535 CrossRef CAS.
  4. A. D. Elbein and R. J. Molyneux, in Iminosugars as Glycosidase Inhibitors, ed. A. E. Stütz, Wiley-VCH, Weinheim, 1999, pp. 216–251 Search PubMed; C. W. Ekhart, M. H. Fechter, P. Hadwiger, E. Mlaker, A. E. Stütz, A. Tauss and T. M. Wrodnigg, in Iminosugars as Glycosidase Inhibitors, ed. A. E. Stütz, Wiley-VCH, Weinheim, 1999, pp. 253–390 Search PubMed; M. Bols, Acc. Chem. Res., 1998, 31, 1 Search PubMed; E. Fenouillet, M. J. Papandreou and I. M. Jones, Virology, 1997, 231, 89 Search PubMed; T. Kolter, Angew. Chem., Int. Ed. Engl., 1997, 36, 1955 CrossRef CAS and references cited therein.
  5. C. Pasquarello, R. Demange and P. Vogel, Bioorg. Med. Chem. Lett., 1999, 9, 793 CrossRef CAS.
  6. B. A. Jones, Y. T. Pan, A. D. Elbein and C. R. Johnson, J. Am. Chem. Soc., 1997, 119, 4856 CrossRef CAS; K. Kraehenbuehl, S. Picasso and P. Vogel, Helv. Chim. Acta, 1998, 81, 1439 CAS; M. A. Leeuwenburgh, S. Picasso, H. S. Overkleeft, G. A. van der Marel, P. Vogel and J. H. van Boom, Eur. J. Org. Chem., 1999, 1185 CrossRef.
  7. See, e.g.: G. D. MacLean, M. B. Bowen-Yacyshyn, J. Samuel, A. Meikle, G. Stuart, J. Nation, S. Poppema, M. Jerry, R. Koganty, T. Wong and B. M. Longenecker, J. Immunother., 1992, 11, 292 Search PubMed; P. D. Rye, N. V. Bovin, E. V. Vlasova and R. A. Walker, Glycobiology, 1995, 5, 385 CAS.
  8. Y.-H. Zhu and P. Vogel, Tetrahedron Lett., 1998, 39, 31 CrossRef CAS.
  9. Y.-H. Zhu and P. Vogel, J. Org. Chem., 1999, 64, 666 CrossRef CAS.
  10. D. L. Comins and A. Dehghani, Tetrahedron Lett., 1992, 33, 6299 CrossRef CAS.
  11. S. Mori, T. Ohno, H. Harada, T. Aoyama and T. Shioiri, Tetrahedron, 1991, 47, 5051 CrossRef CAS.
  12. K. Takai, M. Tagashira, T. Kuroda, K. Oshima, K. Vtimoto and H. Nozaki, J. Am. Chem. Soc., 1986, 108, 6048 CrossRef CAS; D. P. Stamos, X. C. Sheng, S. S. Chen and Y. Kishi, Tetrahedron Lett., 1997, 38, 6355 CrossRef CAS and references cited therein.
  13. Y. Wang, P. G. Goekjian, D. M. Ryckman, W. H. Miller, S. A. Babirad and Y. Kishi, J. Org. Chem., 1992, 57, 482 CrossRef CAS.
  14. F. Rübsam, S. Seck and A. Giannis, Tetrahedron, 1997, 53, 2823 CrossRef; P. Ciapetti, M. Falorni and M. Taddei, Tetrahedron, 1996, 52, 7379 CrossRef CAS.
  15. For the preparation of 18, see: T. Kawai, M. Isobe and S. C. Peters, Aust. J. Chem., 1995, 48, 115 Search PubMed.
  16. J. Cossy, V. Bellosta and M. C. Müller, Tetrahedron Lett., 1992, 33, 5045 CrossRef CAS.
  17. An example of the synthesis of the β-C(1→4)glucopyranoside of 3-deoxy-D-glucose from levoglucosenone was reported by Witczak and co-workers: Z. J. Witczak, R. Chhabra and J. Chojnacki, Tetrahedron Lett., 1997, 38, 2215 Search PubMed.
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