First bile acid-derived chiral dendritic species with nanometric dimensions

Abstract

This paper describes the first synthesis of branched bile acid oligomers.

References

1. (a) The first report of a chiral dendrimer: R. G. Denkewalter, J. F. Kolc and W. J. Lukasavage, U.S. Pat. 4,410,688, 1979; (b) Review on chiral dendrimers: H. W. I. Peerlings and E. W. Meijer, Chem. Eur. J., 1997, 3, 1563; C. W. Thomas and Y. Tor, Chirality, 1998, 10, 53; D. Seebach, P. B. Rheiner, G. Greiveldinger, T. Butz and H. Sellner, Top. Curr. Chem., 1998, 197, 125.
2. E. Buhleier, W. Wehner and F. Vögtle, Synthesis, 1978, 155.
3. D. A. Tomalia, A. M. Naylor and W. A. Goddard III, Angew. Chem., Int. Ed. Engl., 1990, 29, 138; D. A. Tomalia and H. D. Durst, Top. Curr. Chem., 1993, 165, 193; J. Issenberner, R. Moors and F. Vögtle, Angew. Chem., Int. Ed. Engl., 1994, 33, 2413; G. R. Newkome and C. N. Moorefield, Dendrimers, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, J.-M. Lehn, Pergamon, Tarrytown, NY, 1996, vol. 10, p. 777; F. Zeng and S. C. Zimmerman, Chem. Rev., 1997, 97, 1681; D. K. Smith and F. Diederich, Chem. Eur. J., 1998, 4, 1353; M. Fischer and F. Vögtle, Angew. Chem., Int. Ed., 1999, 38, 884.
4. (a) G. R. Newkome, X. Lin and C. D. Weis, Tetrahedron: Asymmetry, 1991, 2, 957; (b) D. Seebach, J.-M. Lapierre, K. Skobridis and G. Greiveldinger, Angew. Chem., Int. Ed. Engl., 1994, 33, 440; (c) P. Murer and D. Seebach, Angew. Chem., Int. Ed. Engl., 1995, 34, 2116; (d) 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; (e) H.-F. Chow and C. C. Mak, J. Chem., Soc., Perkin Trans. 1, 1994, 2223; (f) H.-F. Chow and C. C. Mak, Pure Appl. Chem., 1997, 69, 483; (g) H.-T. Chang, C.-T. Chen, T. Kondo, G. Siuzdak and K. B. Sharpless, Angew. Chem., Int. Ed. Engl., 1996, 35, 182; (h) J. R. McElhanon and D. V. McGrath, J. Am. Chem. Soc., 1998, 120, 1647.
5. R. H. E. Hudson and M. J. Damha, J. Am. Chem. Soc, 1993, 115, 2119.
6. K. Aoi, K. Itoh and M. Okada, Macromolecules, 1995, 28, 5391.
7. U. Maitra and L. J. D'Souza, J. Chem. Soc., Chem. Commun., 1994, 2793; U. Maitra and S. Balasubramanian, J. Chem. Soc., Perkin Trans. 1, 1995, 83; A. P. Davis, R. P. Bonar-law and J. K. M. Sanders, Receptors Based on Cholic Acid, in Comprehensive Supramolecular Chemistry, ed. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vogtle and J.-M. Lehn, Pergamon, Tarrytown, NY, 1996, vol. 4, p. 257; P. A. Brady, R. P. Bonar-law, S. J. Rowan, C. J. Suckling and J. K. M. Sanders, Chem Commun., 1996, 319; Y. Li and J. R. Dias, Chem. Rev., 1997, 97, 283; Y. H. Zhang, M. Akram, H. Y. Liu and X. X. Xhu, Macromol. Chem. Phys., 1998, 199, 1399.
8. C. J. Hawker and J. M. J. Fréchet, J. Am. Chem. Soc., 1990, 112, 7638.
9. The 1-naphthylmethyl group was employed for easier identification of the dendrons in the purification steps, and also in the analysis of the sample by UV and HPLC measurements.
10. The MALDI-TOF MS spectrum showed a peak for 8 at m/z 3143.0 [expected for (M+Na)⁺ 3139.4](Calc. for C₁₉₅H₂₉₂O₃₀: C, 75.15; H, 9.44%. Found: C, 75.33; H, 9.83%). For 9, MALDI-TOF MS spectrum showed a peak for at m/z 4440.6 [expected for (M+Na)⁺= 4436.9](Calc. for C₂₆₃H₃₈₈O₅₄: C, 71.57; H, 8.86. Found: C, 71.89; H, 9.26%).