Stereoselective O-glycosylation reactions employing diphenylphosphinate and propane-1,3-diyl phosphate as anomeric leaving groups

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Vankayalapati Hariprasad, Gurdial Singh and Isabelle Tranoy


Abstract

Glycosidation of tetra-O-benzyl-D-glucose using diphenylphosphinate as the leaving group afforded β-O-linked glycosides as the major products, whilst the use of propane-1,3-diyl phosphate as the leaving group resulted in the exclusive formation of β-O-linked glycoside.


References

  1. A. Varki, Glycobiology, 1993, 3, 97 Search PubMed.
  2. J. Kellerman, F. Lottspeich, A. Henschen and W. Muller-Esterl, Eur. J. Biochem., 1986, 154, 471; S. Hakomori, Cancer Res., 1985, 45, 2405 CAS; J. Montreuil, Adv. Carbohydr. Chem. Biochem., 1980, 37, 157 Search PubMed.
  3. N. Sharon, Trends Biochem. Sci., 1984, 9, 198 CrossRef.
  4. G. J. Boons, Tetrahedron, 1996, 52, 1095 CrossRef CAS; K. Toshima and K. Tatsuta, Chem. Rev., 1993, 93, 1503 CrossRef CAS; K. J. Hale and A. C. Richardson, Carbohydrates, in The Chemistry of Natural Products, ed. K. H. Thomson, Blackie, 1993, ch. 1, p. 1 Search PubMed.
  5. S. Hashimoto, T. Honda and S. Ikegami, Tetrahedron Lett., 1991, 32, 1653 CrossRef CAS; S. Hashimoto, T. Honda and S. Ikegami, Heterocycles, 1990, 30, 775 CAS; S. Hashimoto, T. Honda and S. Ikegami, Chem. Pharm. Bull., 1990, 38, 2323 CAS; S. Hashimoto, T. Honda and S. Ikegami, J. Chem. Soc., Chem. Commun., 1989, 685 RSC.
  6. H. Harada, S. Hashimoto, T. Honda and S. Ikegami, Tetrahedron Lett., 1992, 33, 3523 CrossRef; S. Hashimoto, T. Honda and S. Ikegami, Tetrahedron Lett., 1990, 31, 4769 CrossRef CAS.
  7. T. Inazu and T. Yamanoi, Chem. Lett., 1990, 849; T. Inazu and T. Yamanoi, Chem. Lett., 1989, 69 CAS; T. Inazu, H. Hosokawa and Y. Satoh, Chem. Lett., 1985, 297 CAS.
  8. R. Ramage, D. Hopton, M. J. Parrott, G. W. Kenner and G. A. Moore, J. Chem. Soc., Perkin Trans. 1, 1984, 1357 RSC and references cited therein.
  9. T. R. Fukuto and R. L. Metcalf, J. Med. Chem., 1965, 8, 759 CrossRef CAS; F. Ramirez, H. Tsuboi, H. Okazaki and R. F. Marecek, Tetrahedron Lett., 1982, 23, 5375 CrossRef CAS; R. N. Hunston, S. A. Jones, C. McGuigan, T. Richard, J. Balzarini and E. De Clercq, J. Med. Chem., 1984, 27, 440 CrossRef CAS; E. L. Eliel, S. Chandraserkaran, L. E. Carpenter II and J. G. Verkade, J. Am. Chem. Soc., 1986, 108, 6651 CrossRef CAS.
  10. A. Esswein and R. R. Schmidt, Liebigs Ann. Chem., 1988, 675 Search PubMed.
  11. K. Bock and C. Pedersen, Adv. Carbohydr. Chem. Biochem., 1983, 41, 27 Search PubMed.
  12. S. Houdier and P. J. A. Vottéro, Tetrahedron Lett., 1993, 34, 3283 CrossRef CAS for the α-isomer of this compound, see: P. G. Garegg, J.-L. Maloisel and S. Oscarson, Synthesis, 1995, 409 Search PubMed.
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