Dendronized polyacrylates with glucose units in the periphery

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Andrea Zistler, Sabine Koch and A. Dieter Schlüter


Abstract

The synthesis of dendritic building blocks (dendrons) of the first (G-1) and second generation (G-2) with peripheral acetyl-protected glucose moieties is reported. The dendrons can be selectively deprotected at the focal point and the resulting carboxylic acids then attached to an acrylic acid derivative to furnish dendronized G-1 and G-2 macromonomers. Their radically initiated polymerization leads to dendronized polyacrylates with two and four surface glucose units per repeat unit.


References

  1. For a comprehensive treatment of spherically shaped dendrimers see: G. R. Newkome, C. N. Moorefield and F. Vögtle, Dendritic Molecules—Concepts, Syntheses, Perspectives, VCH, Weinheim, 1996 Search PubMed.
  2. G. R. Newkome, C. N. Moorefield, G. R. Baker, A. L. Johnson and R. K. Behera, Angew. Chem., Int. Ed. Engl., 1991, 30, 1176 CrossRef.
  3. (a) S. Stevelmans, J. C. M. van Hest, J. F. G. A. Jansen, D. A. F. J. van Boxtel, E. M. M. de Brabander-van den Berg and E. W. Meijer, J. Am. Chem. Soc., 1996, 118, 7398 CrossRef CAS; (b) J. F. G. A. Jansen, E. M. M. de Brabander-van den Berg and E. W. Meijer, Science, 1994, 266, 1226 CrossRef CAS; (c) J. F. G. A. Jansen, H. W. I. Peerlings, E. M. M. de Brabander-van den Berg and E. W. Meijer, Angew. Chem., Int. Ed. Engl., 1995, 34, 1206 CrossRef CAS.
  4. P. Murer and D. Seebach, Angew. Chem., Int. Ed. Engl., 1995, 34, 2116 CrossRef CAS.
  5. (a) S. A. DeFrees and F. C. A. Gaeta, J. Am. Chem. Soc., 1993, 115, 7549 CrossRef CAS; (b) E. S. Litscher, K. Juntunen, A. Seppo, L. Penttilä, R. Renkonen and P. M. Wassarman, Biochemistry, 1995, 34, 4662 CrossRef CAS; (c) K. H. Mortell, R. V. Weatherman and L. L. Kiessling, J. Am. Chem. Soc., 1996, 118, 2297 CrossRef CAS; (d) G. B. Sigal, M. Mammen, G. Dahmann and G. M. Whitesides, J. Am. Chem. Soc., 1996, 118, 3789 CrossRef.
  6. (a) Y. C. Lee, R. T. Lee, K. Rice, Y. Ichikawa and T.-C. Wong, Pure Appl. Chem., 1991, 63, 499 CAS; (b) R. Lee and Y. C. Lee, Neoglycoconjugates, ed. Y. C. Lee and R. Lee, Academic Press, San Diego, 1994, p. 23 Search PubMed.
  7. (a) R. Roy, D. Zanini, S. J. Meunier and A. Romanowska, J. Chem. Soc., Chem. Commun., 1993, 1869 RSC; (b) R. Roy, W. K. C. Park, Q. Wu and S.-N. Wang, Tetrahedron Lett., 1995, 36, 4377 CrossRef CAS; (c) D. Zanini, W. K. C. Park and R. Roy, Tetrahedron Lett., 1995, 36, 7383 CrossRef CAS; (d) R. Roy, Modern Methods in Carbohydrate Synthesis, ed. S. H. Khan and R. A. O'Neill, Harwood, Amsterdam, 1996, p. 378 Search PubMed; (e) D. Zanini and R. Roy, J. Am. Chem. Soc., 1997, 119, 2088 CrossRef CAS.
  8. K. Aoi, K. Itoh and M. Okada, Macromolecules, 1995, 28, 5391 CrossRef CAS.
  9. T. K. Lindhorst and C. Kieburg, Angew. Chem., Int. Ed. Engl., 1996, 35, 1953 CrossRef CAS.
  10. (a) P. R. Ashton, S. E. Boyd, C. L. Brown, N. Jayaraman, S. A. Nepogodiev and J. F. Stoddart, Chem. Eur. J., 1996, 2, 1115 CrossRef CAS; (b) P. R. Ashton, S. E. Boyd, C. L. Brown, N. Jayaraman and J. F. Stoddart, Angew. Chem., Int. Ed. Engl., 1997, 36, 756; (c) P. R. Ashton, S. E. Boyd, C. L. Brown, N. Jayaraman, S. A. Nepogodiev, E. W. Meijer, H. W. I. Peerlings and J. F. Stoddart, Chem. Eur. J., 1997, 3, 974 CrossRef CAS.
  11. A. D. Schlüter, Top. Curr. Chem., 1998, Vol. Dendrimers, 165 Search PubMed.
  12. (a) W. Stocker, B. L. Schürmann, J. P. Rabe, S. Förster, P. Lindner, I. Neubert and A. D. Schlüter, Adv. Mater., 1998, 10, 793 CrossRef CAS; (b) W. Stocker, B. Karakaya, B. L. Schürmann, J. P. Rabe and A. D. Schlüter, J. Am. Chem. Soc., 1998, 120, 7691 CrossRef CAS.
  13. I. Neubert and A. D. Schlüter, Macromolecules, 1998, 31, 9372 CrossRef CAS.
  14. A dendronized polyacrylate without functional groups in the periphery has also been reported: I. Neubert, R. Klopsch, W. Claussen and A. D. Schlüter, Acta Polym., 1996, 47, 455 Search PubMed.
  15. (a) R. Klopsch, S. Koch and A. D. Schlüter, Eur. J. Org. Chem., 1998, 1275 CrossRef CAS; (b) A. Ingerl, I. Neubert, R. Klopsch and A. D. Schlüter, Eur. J. Org. Chem., 1998, 2551 CrossRef CAS.
  16. M. Elofsson, B. Walse and J. Kihlberg, Tetrahedron Lett., 1991, 32, 7613 CrossRef CAS.
  17. (a) J. C. Sheehan, J. Preston and P. A. Cruickshank, J. Am. Chem. Soc., 1965, 87, 2492 CrossRef CAS; (b) J. C. Sheehan and S. L. Ledis, J. Am. Chem. Soc., 1973, 95, 875 CrossRef CAS; (c) W. König and R. Geiger, Chem. Ber., 1970, 103, 788 CrossRef CAS.
  18. (a) G. Wulff, J. Schmid and T. P. Venhoff, Macromol. Chem. Phys., 1996, 197, 259 CrossRef CAS; (b) G. Wulff, L. Zhu and H. Schmidt, Macromolecules, 1997, 30, 4533 CrossRef CAS.
  19. (a) X. Chen, J. S. Dordick and D. G. Rethwisch, Macromolecules, 1995, 28, 6014 CrossRef CAS; (b) B. D. Martin, S. A. Ampofo, R. J. Lindhardt and J. S. Dordick, Macromolecules, 1992, 25, 7081 CrossRef CAS; (c) X. Chen, B. D. Martin, T. K. Neubauer, R. J. Lindhardt, J. S. Dordick and D. G. Rethwisch, Carbohydr. Polym., 1995, 28, 15 CrossRef CAS.
  20. (a) S. Kimura and M. Imoto, Makromol. Chem., 1961, 50, 155 CrossRef CAS; (b) S. Kimura and K. Hirai, Makromol. Chem., 1962, 58, 232 CrossRef CAS; (c) W. A. P. Black, E. T. Dewar and D. Rutherford, J. Chem. Soc., 1963, 4433 RSC; (d) A. Spaltenstein and G. M. Whitesides, J. Am. Chem. Soc., 1991, 113, 686 CrossRef CAS.
  21. The rest of the material was monomer.
  22. See ref. 13. Note that the relative molecular mass of G-1 acrylate 14 is in the range of G-2 macromonomers described there.
  23. (a) V. Percec, C.-H. Ahn and B. Barboiu, J. Am. Chem. Soc., 1997, 119, 12978 CrossRef CAS; (b) V. Percec, C.-H. Ahn, W.-D. Cho, A. M. Jamieson, J. Kim, T. Leman, M. Schmidt, M. Gerle, M. Möller, S. A. Prokhorova, S. S. Sheiko, S. Z. D. Cheng, A. Zhang, G. Ungar and D. J. P. Yeardley, J. Am. Chem. Soc., 1998, 120, 8619 CrossRef CAS.
  24. S. Förster, I. Neubert, A. D. Schlüter and P. Lindner, Macromolecules, submitted Search PubMed.
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