Alkenyl O- and C-glycopyranoside homodimerization by olefin metathesis reaction

Abstract

Using ruthenium-catalyzed olefin metathesis, several O- and C-allyl and O-pentenyl D-galactopyranoside and lactoside homodimers were prepared in high yields.

References

1. R. Roy, in Carbohydrate Chemistry, ed. G. J. Boons, Chapman & Hall, UK, 1998, p. 243; R. Roy, Curr. Opin. Struct. Biol., 1996, 6, 692; L. L. Kiessling and N. L. Pohl, Chem. Biol., 1996, 3, 71; N. V. Bovin and H.-J. Gabius, Chem. Soc. Rev., 1995, 24, 413.
2. Y. C. Lee and R. T. Lee, Acc. Chem. Res., 1995, 28, 322; A. Lubineau, S. Escher, J. Alais and D. Bonnaffé, Tetrahedron Lett., 1997, 38, 4087; R. J. Patch, H. Chen and C. R. Pandit, J. Org. Chem., 1997, 62, 1543; D. Pagé and R. Roy, Bioorg. Med. Chem. Lett., 1996, 6, 1765; S. A. DeFrees, W. Kosch, W. Way, J. C. Paulson, S. Sabesan, R. L. Halcomb, D.-H. Huang, Y. Ichikawa and C.-H. Wong, J. Am. Chem. Soc., 1995, 117, 66.
3. R. Roy, Top. Curr. Chem., 1997, 187, 241; D. Zanini and R. Roy, in Carbohydrate Mimics: Concepts and Methods, ed. Y. Chapleur, Verlag Chemie, Weinheim, Germany, 1998, p. 385; N. Jayaraman, S. A. Nepogodiev and J. F. Stoddart, Chem. Eur. J., 1997, 3, 1193.
4. K. J. Yarema and C. R. Bertozzi, Curr. Opin. Chem. Biol., 1998, 2, 49; R. Roy, in Carbohydrates in Drug Design, ed. Z. J. Witczak and K. A. Nieforth, Marcel Dekker, NY, 1997, p. 83.
5. J. A. Wells, Curr. Opin. Cell Biol., 1994, 6, 163; C.-H. Heldin, Cell, 1995, 80, 213; D. L. Boger and W. Chai, Tetrahedron, 1998, 54, 3955; S. T. Diver and S. L. Schreiber, J. Am. Chem. Soc., 1997, 119, 5106.
6. P. Velupillai and D. A. Harn, Proc. Natl. Acad. Sci. U.S.A., 1994, 91, 18; I. Takata, K. Chida, M. R. Gordon, Q. N. Myrvik, M. J. Ricardo, Jr. and L. S. Kucera, J. Leukocyte Biol., 1987, 41, 248; E. J. Gordon, W. J. Sanders and L. L. Kiessling, Nature, 1998, 392, 30.
7. S. T. Nguyen, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1993, 115, 9858; E. L. Dias, S. T. Nguyen and R. H. Grubbs, J. Am. Chem. Soc., 1997, 119, 3887; P. Schwab, R. H. Grubbs and J. W. Ziller, J. Am. Chem. Soc., 1996, 118, 100; M. Schuster and S. Blechert, Angew. Chem., Int. Engl., 1997, 36, 2036; R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; R. H. Grubbs, S. J. Miller and G. C. Fu, Acc. Chem. Res., 1995, 28, 446.
8. R. R. Schrock, S. J. Murdzek, G. C. Bagan, M. Dimare and M. O'Regan, J. Am. Chem. Soc., 1990, 112, 3875; G. C. Bagan, J. H. Oskam, H.-N. Cho, L. Y. Park and R. R. Schrock, J. Am. Chem. Soc., 1991, 113, 6899.
9. For examples in RCM: H. S. Overkleeft and U. K. Pandit, Tetrahedron Lett., 1996, 37, 547; A. Furstner and T. Muller, J. Org. Chem., 1998, 63, 424; P. A. Van Hooft, M. A. Leeuwenburgh, H. S. Overkleeft, G. A. Van der Marel, C. A. A. van Boeckel and J. H. van Boom, Tetrahedron Lett., 1998, 39, 6061 examples in CM: J. Feng, M. Schuster and S. Blechert, Synlett, 1997, 129; M. Schuster, N. Lucas and S. Blechert, Chem. Commun., 1997, 823 examples in ROMP: K. H. Mortell, M. Gingras and L. L. Kiessling, J. Am. Chem. Soc., 1994, 116, 12053; C. Fraser and R. H. Grubbs, Macromolecules, 1995, 28, 7248; K. Nomura and R. R. Schrock, Macromolecules, 1996, 29, 540.
10. G. Descotes, J. Ramza, J.-M. Basset and S. Pagano, Tetrahedron Lett., 1994, 35, 7379; J. Ramza, G. Descotes, J. M. Basset and A. Mutch, J. Carbohydr. Chem., 1996, 15, 125.
11. E. Breitmaier and W. Voelter, Carbon-13 NMR Spectroscopy. High Resolutions Methods and Applications in Organic Chemistry and Biochemistry, VCH, New York, 1987, pp. 192–195.
12. A. Giannis and K. Sandhoff, Tetrahedron Lett., 1985, 26, 1479.
13. T. Uchiyama, T. J. Woltering, W. Wong, C. C. Lin, T. Kajimoto, M. Takebayashi, G. W. Schmidt, T. Asakura, M. Noda and C. H. Wong, Bioorg. Med. Chem., 1996, 4, 1149.