Stereoselective α-glycosidation using FeCl3 as a Lewis acid catalyst

(Note: The full text of this document is currently only available in the PDF Version )

Swapan K. Chatterjee and Peter Nuhn


Abstract

A simplified procedure for the stereoselective α-glycosidation of peracetylated sugars, carrying a participating group at C2, with aliphatic alcohols in the presence of FeCl3 as a Lewis acid is described.


References

  1. G. Bendas, F. Wilhelm, W. Richter and P. Nuhn, Eur. J. Pharm. Sci., 1996, 4, 211 CrossRef CAS; P. Nuhn, T. Pfaff, G. Bendas, F. Wilhelm and S. K. Chatterjee, Arch. Pharm., 1994, 327, 429 Search PubMed; A. Engel, G. Bendas, F. Wilhelm, M. Mannova, M. Ausborn and P. Nuhn, Int. J. Pharm., 1994, 107, 99 CrossRef CAS; A. Engel, K. Augsten, F. Wilhelm, S. K. Chatterjee and P. Nuhn, Arch. Pharm., 1993, 326, 648 Search PubMed; G. Förster, O. de la Cruz Rodriguez, G. Bendas and P. Nuhn, Prog. Colloid Polym. Sci., 1995, 98, 201 Search PubMed.
  2. G. Wulff and G. Röhle, Angew Chem., Int. Ed. Engl., 1974, 13, 157 CrossRef CAS; H. Paulsen, ibid., 1982, 21, 155 Search PubMed; R. R. Schmidt, ibid., 1986, 25, 212 Search PubMed; J. Thiem, Annu. Rep. Prog. Chem., Sect. B, 1985, 81, 311 RSC; K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503 CrossRef CAS.
  3. F. Wilhelm, S. K. Chatterjee, B. Rattay, P. Nuhn, R. Benecke and J. Ortwein, Liebigs Ann., 1995, 1673 CAS.
  4. M. Tanaka, M. Okita and I. Yamatsu, Carbohydr. Res., 1993, 241, 81 CrossRef CAS.
  5. D. Kahne, D. Yang, J. J. Lim, R. Miller and E. Paguaga, J. Am. Chem. Soc., 1988, 110, 8716 CrossRef CAS.
  6. S. Koto, N. Morishima, Y. Miyata and S. Zen, Bull. Chem. Soc. Jpn., 1976, 49, 2639 CAS.
  7. (a) S. Koto, N. Morishima, R. Kawahara, K. Ishikawa and S. Zen, Bull. Chem. Soc. Jpn., 1982, 55, 1092 CAS; (b) P. Nuhn and G. Wagner, Z. Chem., 1967, 7, 154 CAS; (c) N. Ikemoto, O. K. Kim, L.-C. Lo, V. Satyanarayana, M. Chang and K. Nakanishi, Tetrahedron Lett., 1992, 33, 4295 CrossRef CAS.
  8. F. Dasgupta, P. P. Singh and H. C. Srivastava, Carbohydr. Res., 1980, 80, 346 CrossRef CAS; V. Ferrieres, J.-N. Bertho and D. Plusquellee, Tetrahedron Lett., 1995, 36, 2753 CrossRef.
  9. H. Leffler and C. Svanborg-Eden, FEMS Microbiol. Lett., 1980, 8, 127 CrossRef CAS; G. Källenius, R. Möllby, S. B. Svenson, J. Winberg, A. Lundblad, S. Svenssen and B. Cedergren, ibid., 1980, 7, 297 Search PubMed.
  10. M. Naiki and M. Kato, Vox Sang., 1979, 37, 30 CAS; R. R. Race and R. Sanger, Blood Groups in Man, 6th edn., Blackwell, Oxford, 1975 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.