Peptide templated glycosidic bond formation: a new strategy for oligosaccharide synthesis†

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Richard J. Tennant-Eyles, Antony J. Fairbanks and Benjamin G. Davis


Abstract

Glycosidation reactions performed between glycosyl donors and acceptors covalently linked to a peptide template produced increased regio- and stereo-selectivities, which were dependent on the nature of the peptide, and which may be rationalised by simple molecular modelling.


References

  1. W. Koenigs and E. Knorr, Chem. Ber., 1901, 34, 957 Search PubMed.
  2. For some recent reviews and books see: K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503 Search PubMed; G.-J. Boons, Tetrahedron, 1996, 52, 1095 CrossRef CAS; Modern Methods in Carbohydrate Synthesis, ed. S. H. Khan and R. A. O'Neill, Harwood Academic, Amsterdam, 1996 CrossRef CAS; Preparative Carbohydrate Chemistry, ed. S. Hanessian, Marcel Dekker, New York, 1997 CrossRef CAS.
  3. G. Stork and G. Kim, J. Am. Chem. Soc., 1992, 114, 1087 CrossRef.
  4. F. Barresi and O. Hindsgaul, Can. J. Chem., 1994, 72, 1447 CAS; F. Barresi and O. Hindsgaul, Synlett, 1992, 759 CrossRef CAS; F. Barresi and O. Hindsgaul, J. Am. Chem. Soc., 1991, 113, 9376 CrossRef CAS.
  5. Y. Ito, Y. Ohnishi, T. Ogawa and Y. Nakahara, Synlett, 1998, 1102 CAS; A. Dan, Y. Ito and T. Ogawa, J. Org. Chem., 1995, 60, 4680 CrossRef CAS; Y. Ito and T. Ogawa, Angew. Chem., Int. Ed. Engl., 1994, 33, 1765 CrossRef.
  6. T. Zeigler, G. Lemanski and A. Rakoczy, Tetrahedron Lett., 1995, 36, 8973 CrossRef CAS; T. Zeigler and R. Lau, Tetrahedron Lett., 1995, 36, 1417 CrossRef CAS; R. Lau, G. Schülle, U. Schwaneberg and T. Zeigler, Liebigs Ann., 1995, 1475; H. Yamada, K. Imamura and T. Takahashi, Tetrahedron Lett., 1997, 36, 391 CrossRef CAS; S. Valverde, A. M. Gömez, A. Hernández, B. Herradón and J. C. López, J. Chem. Soc., Chem. Commun., 1995, 2005 RSC.
  7. R. J. Tennant-Eyles and A. J. Fairbanks, Tetrahedron: Asymmetry, 1999, 10, 391 CrossRef CAS.
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