Synthesis of pseudo-oligosaccharides by a sequence of yne-ene cross metathesis and Diels–Alder reaction

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Stephan C. Schürer and Siegfried Blechert


Abstract

Various pseudo oligosaccharides were prepared by a combination of selective yne-ene cross metathesis and Diels–Alder reaction from readily available monosaccharide building blocks.


References

  1. For references see: R. A. Dwek, Chem. Rev., 1996, 96, 683 Search PubMed; R. Roy, in Carbohydrate Chemistry, ed. G. J. Boons, Chapman and Hall, UK, 1998, p. 243 CrossRef CAS; Glycosciences, Status and Perspectives; ed. H.-J. Gabius and S. Gabius, Chapman and Hall, Weinheim, 1997, p. 291 CrossRef CAS; S. Hakamori and Y. Zhang, Chem. Biol., 1997, 4, 97 CrossRef CAS; R. Roy, Curr. Opin. Struct. Biol., 1996, 6, 692 Search PubMed; L. L. Kiessling and N. L. Pohl, Chem. Biol., 1996, 3, 71 Search PubMed; N. J. Bovin and H.-J. Gabius, Chem. Soc. Rev., 1995, 24, 413.
  2. For recent references see: K. J. Yarema and C. R. Bertozzi, Curr. Opin. Chem. Biol., 1998, 2, 49 Search PubMed; Carbohydrates in Drug Design, ed. Z. J. Witczak and K. A. Nieforth, Marcel Decker, New York, 1997 CrossRef CAS.
  3. General reviews on olefin metathesis: R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413 Search PubMed; S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371 CrossRef CAS; M. Schuster and S. Blechert, Angew. Chem., 1997, 109, 2124 RSC; Angew. Chem., Int. Ed. Engl., 1997, 36, 2036 CrossRef.
  4. P. Schwab, M. B. France, J. W. Ziller and R. H. Grubbs, Angew. Chem., 1995, 107, 2179 CrossRef; Angew. Chem., Int. Ed. Engl., 1995, 34, 2039 Search PubMed.
  5. For recent examples see: O. Sellier, P. Van de Weghe, D. Le Nouen, C. Strehler and J. Eustache, Tetrahedron Lett., 1999, 40, 853 Search PubMed; D. J. Holt, W. D. Barker, P. R. Jenkins, D. L. Davies, S. Garrat, J. Fawcett, D. R. Russel and S. Ghosh, Angew. Chem., 1998, 110, 3486 CrossRef CAS; Angew. Chem. Int. Ed., 1998, 37, 3298 CrossRef; H. S. Overkleeft, P. Bruggeman and U. K. Pandit, Tetrahedron Lett., 1998, 39, 3869 CrossRef; H. Ovaa, M. A. Leeuwenburgh, H. S. Overkleeft, G. A. van der Marel and J. H. van Boom, Tetrahedron Lett., 1998, 39, 3025 Search PubMed; A. Fürstner and T. Müller, J. Org. Chem., 1998, 63, 424 CrossRef CAS; F. E. Ziegler and Y. Wang, J. Org. Chem., 1998, 63, 426 CrossRef CAS.
  6. K. Nomura and R. R. Schrock, Macromolecules, 1996, 29, 540 CrossRef CAS; C. Fraser and R. H. Grubbs, Macromolecules, 1995, 28, 7248 CrossRef CAS; K. H. Mortell, M. Gingras and L. L. Kiessling, J. Am. Chem. Soc., 1994, 116, 12053 CrossRef CAS.
  7. R. Dominique, S. K. Das and R. Roy, Chem. Commun., 1998, 2437 RSC.
  8. J. Feng, M. Schuster and S. Blechert, Synlett, 1997, 129 CAS; M. Schuster, N. Lucas and S. Blechert, Chem. Commun., 1997, 823 RSC; M. Schuster and S. Blechert, Tetrahedron Lett., 1998, 39, 2295 CrossRef CAS.
  9. R. Stragies, M. Schuster and S. Blechert, Angew. Chem., 1997, 109, 2628; Angew. Chem., Int. Ed. Engl., 1997, 36, 2518 Search PubMed.
  10. W. R. Roush and D. A. Barda, J. Am. Chem. Soc., 1997, 119, 7402 CrossRef CAS.
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