Synthesis and properties of O-glycosyl calix[4]arenes (calixsugars)

Chemistry - A European Journal

Volumn 3, Issue 11, 1997, Pages 1774-1782

  Dondoni, Alessandro ^a   Marra, Alberto ^a   Scherrmann, Marie Christine ^a,c   Casnati, Alessandro ^b   Sansone, Francesco ^b   Ungaro, Rocco ^b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

^c UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

Calixarenes; Carbohydrates; Glycosylations; Host guest chemistry; Mitsunobu reaction

Indexed keywords

EID: 0030831718     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/chem.19970031108     Document Type: Article

References (105)

1. a) C. D. Gutsehe in Calixarenes, Monograph in Supramolecular Chemistry, Vol. 1 (Ed.: J. F. Stoddart), Royal Society of Chemistry, Cambridge, 1989;
2. b) Calixarenes, a Versatile Class of Macrocyclic Compounds (Eds.: J. Vicens, V. Böhmen), Kluwer, Dordrecht, 1991;
3. c) A. Pochini, R. Ungaro, Comprehensive Supramolecular Chemistry, Pergamon Press, Oxford, 1996.
4. J. D. Kilburn, H. K. Patel, Contemp. Org. Synth. 1994, 1, 259-286;
5. b) H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1438; Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436.
6. b) H.-J. Schneider, Angew. Chem. 1991, 103, 1419-1438; Angew. Chem. Int. Ed. Engl. 1991, 30, 1417-1436.
7. This topic has been discussed in recent reviews: a) V. Böhmer, Angew. Chem. 1995, 107, 785-817; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745; b) M. Takeshita, S. Shinkai, Bull. Chem. Soc. Jpn. 1995, 68, 1088-1097; c) P. Lhoták, S. Shinkai, J. Synth. Org. Chem. Jpn. 1995, 53, 963-974; d) D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24.
8. This topic has been discussed in recent reviews: a) V. Böhmer, Angew. Chem. 1995, 107, 785-817; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745; b) M. Takeshita, S. Shinkai, Bull. Chem. Soc. Jpn. 1995, 68, 1088-1097; c) P. Lhoták, S. Shinkai, J. Synth. Org. Chem. Jpn. 1995, 53, 963-974; d) D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24.
9. This topic has been discussed in recent reviews: a) V. Böhmer, Angew. Chem. 1995, 107, 785-817; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745; b) M. Takeshita, S. Shinkai, Bull. Chem. Soc. Jpn. 1995, 68, 1088-1097; c) P. Lhoták, S. Shinkai, J. Synth. Org. Chem. Jpn. 1995, 53, 963-974; d) D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24.
10. This topic has been discussed in recent reviews: a) V. Böhmer, Angew. Chem. 1995, 107, 785-817; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745; b) M. Takeshita, S. Shinkai, Bull. Chem. Soc. Jpn. 1995, 68, 1088-1097; c) P. Lhoták, S. Shinkai, J. Synth. Org. Chem. Jpn. 1995, 53, 963-974; d) D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24.
11. This topic has been discussed in recent reviews: a) V. Böhmer, Angew. Chem. 1995, 107, 785-817; Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745; b) M. Takeshita, S. Shinkai, Bull. Chem. Soc. Jpn. 1995, 68, 1088-1097; c) P. Lhoták, S. Shinkai, J. Synth. Org. Chem. Jpn. 1995, 53, 963-974; d) D. Diamond, M. A. McKervey, Chem. Soc. Rev. 1996, 15-24.
12. For a review, see: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719-725. See also: a) P. Timmerman, W. Verboom, F. C. van Veggel, J. P. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437-2440; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) W. Wasikiewicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, ibid. 1994, 106, 230-232 and 1994, 33, 214-216; c) P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron 1996, 52, 12399-12408.
13. For a review, see: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719-725. See also: a) P. Timmerman, W. Verboom, F. C. van Veggel, J. P. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437-2440; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) W. Wasikiewicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, ibid. 1994, 106, 230-232 and 1994, 33, 214-216; c) P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron 1996, 52, 12399-12408.
14. For a review, see: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719-725. See also: a) P. Timmerman, W. Verboom, F. C. van Veggel, J. P. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437-2440; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) W. Wasikiewicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, ibid. 1994, 106, 230-232 and 1994, 33, 214-216; c) P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron 1996, 52, 12399-12408.
15. For a review, see: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719-725. See also: a) P. Timmerman, W. Verboom, F. C. van Veggel, J. P. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437-2440; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) W. Wasikiewicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, ibid. 1994, 106, 230-232 and 1994, 33, 214-216; c) P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron 1996, 52, 12399-12408.
16. For a review, see: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719-725. See also: a) P. Timmerman, W. Verboom, F. C. van Veggel, J. P. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437-2440; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) W. Wasikiewicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, ibid. 1994, 106, 230-232 and 1994, 33, 214-216; c) P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron 1996, 52, 12399-12408.
17. For a review, see: Z. Asfari, J. Weiss, J. Vicens, Synlett 1993, 719-725. See also: a) P. Timmerman, W. Verboom, F. C. van Veggel, J. P. van Duynhoven, D. N. Reinhoudt, Angew. Chem. 1994, 106, 2437-2440; Angew. Chem. Int. Ed. Engl. 1994, 33, 2345-2348; b) W. Wasikiewicz, G. Rokicki, J. Kielkiewicz, V. Böhmer, ibid. 1994, 106, 230-232 and 1994, 33, 214-216; c) P. Lhoták, M. Kawaguchi, A. Ikeda, S. Shinkai, Tetrahedron 1996, 52, 12399-12408.
18. a) T. Nagasaki, H. Fujishima, S. Shinkai, Chem. Lett. 1994, 989-992;
19. b) D. M. Rudkevich, W. Verboom, D. N. Reinhoudt, Tetrahedron Lett. 1994, 35, 7131-7134.
20. A. Casnati, A. Pochini, R. Ungaro, C. Bocchi, F. Ugozzoli, R. J. M. Egberink, H. Struijk, R. Lugtenberg, F. de Jong, D. N. Reinhoudt, Chem. Eur. J. 1996, 2, 436-445 and references therein.
21. 60 fullerene moiety has been covalently linked to a calix[8]arene derivative, see: M. Takeshita, T. Suzuki, S. Shinkai, J. Chem. Soc. Chem. Commun. 1994, 2587-2588.
22. a) F. D'Alessandro, F. G. Gulino, G. Impellizzeri, G. Pappalardo, E. Rizzarelli, D. Sciotto, G. Vecchio, Tetrahedron Lett. 1994, 35, 629-632;
23. b) E. van Dienst, B. H. M. Snellink, I. von Piekartz, J. F. J. Engbersen, D. N. Reinhoudt, J. Chem. Soc. Chem. Commun. 1995, 1151-1152.
24. A. Casnati, M. Fabbi, N. Pelizzi, A. Pochini, F. Sansone, R. Ungaro, Bioorg. Med. Chem. Lett. 1996, 6, 2699-2704.
25. For recent reviews, see: a) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373-380; b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922.
26. For recent reviews, see: a) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373-380; b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922.
27. For recent reviews, see: a) R. U. Lemieux, Acc. Chem. Res. 1996, 29, 373-380; b) T. D. James, K. R. A. S. Sandanayake, S. Shinkai, Angew. Chem. 1996, 108, 2038-2050; Angew. Chem. Int. Ed. Engl. 1996, 35, 1910-1922.
28. Reviews dealing with glycobiology: a) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321-327; b) R. A. Dwek, Chem. Rev. 1996, 96, 683-720.
29. Reviews dealing with glycobiology: a) Y. C. Lee, R. T. Lee, Acc. Chem. Res. 1995, 28, 321-327; b) R. A. Dwek, Chem. Rev. 1996, 96, 683-720.
30. Synthetic receptors for carbohydrate recognition are: a) cholaphanes (A. P. Davis, Chem. Soc. Rev. 1993, 22, 243-253, and references therein); b) glycophanes (J. Jiménez-Barbero, E. Junquera, M. Martin-Pastor, S. Sharma, C. Vicent, S. Penadés, J. Am. Chem. Soc. 1995, 117, 11198-11204); c) steroid-capped porphyrins (R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271); d) binaphthyl-derived cyclophanes (U. Neidlein, F. Diederich, Chem. Commun. 1996, 1493-1494 and references therein).
31. Synthetic receptors for carbohydrate recognition are: a) cholaphanes (A. P. Davis, Chem. Soc. Rev. 1993, 22, 243-253, and references therein); b) glycophanes (J. Jiménez-Barbero, E. Junquera, M. Martin-Pastor, S. Sharma, C. Vicent, S. Penadés, J. Am. Chem. Soc. 1995, 117, 11198-11204); c) steroid-capped porphyrins (R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271); d) binaphthyl-derived cyclophanes (U. Neidlein, F. Diederich, Chem. Commun. 1996, 1493-1494 and references therein).
32. Synthetic receptors for carbohydrate recognition are: a) cholaphanes (A. P. Davis, Chem. Soc. Rev. 1993, 22, 243-253, and references therein); b) glycophanes (J. Jiménez-Barbero, E. Junquera, M. Martin-Pastor, S. Sharma, C. Vicent, S. Penadés, J. Am. Chem. Soc. 1995, 117, 11198-11204); c) steroid-capped porphyrins (R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271); d) binaphthyl-derived cyclophanes (U. Neidlein, F. Diederich, Chem. Commun. 1996, 1493-1494 and references therein).
33. Synthetic receptors for carbohydrate recognition are: a) cholaphanes (A. P. Davis, Chem. Soc. Rev. 1993, 22, 243-253, and references therein); b) glycophanes (J. Jiménez-Barbero, E. Junquera, M. Martin-Pastor, S. Sharma, C. Vicent, S. Penadés, J. Am. Chem. Soc. 1995, 117, 11198-11204); c) steroid-capped porphyrins (R. P. Bonar-Law, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 259-271); d) binaphthyl-derived cyclophanes (U. Neidlein, F. Diederich, Chem. Commun. 1996, 1493-1494 and references therein).
34. a) A. Marra, M.-C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533-2535; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481;
35. a) A. Marra, M.-C. Scherrmann, A. Dondoni, A. Casnati, P. Minari, R. Ungaro, Angew. Chem. 1994, 106, 2533-2535; Angew. Chem. Int. Ed. Engl. 1994, 33, 2479-2481;
36. b) A. Marra, A. Dondoni, F. Sansone, J. Org. Chem. 1996, 61, 5155-5158.
37. Calix[4]arene 1a is commercially available. However, it can be prepared in multigram scale from 1b according to: A. Arduini, A. Casnati in Macrocycle Synthesis, a Practical Approach (Ed.: D. Park), Oxford University Press, Oxford, 1996, pp. 145-173.
38. a) M. Yamaguchi, A. Horiguchi, A. Fukuda, T. Minami, J. Chem. Soc. Perkin Trans. 1 1990, 1079-1082;
39. b) S. Grabley, M. Gareis, W. Böckers, J. Thiem, Synthesis 1992, 1078-1080;
40. c) K. J. Jensen, M. Meldal, K. Bock, J. Chem. Soc. Perkin Trans. 1 1993, 2119-2129;
41. d) T. Yamanoi, A. Fujioka, T. Inazu, Bull. Chem. Soc. Jpn. 1994, 67, 1488-1491;
42. e) F. Clerici, M. L. Gelmi, S. Mottadelli, J. Chem. Soc. Perkin Trans. 1 1994, 985-988.
43. O. Mitsunobu, Synthesis 1981, 1-28. For a recent review, see: D. L. Hughes, Org. Prep. Proced. Int. 1996, 28, 127-164.
44. O. Mitsunobu, Synthesis 1981, 1-28. For a recent review, see: D. L. Hughes, Org. Prep. Proced. Int. 1996, 28, 127-164.
45. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
46. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
47. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
48. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
49. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
50. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
51. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
52. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
53. Previous applications of the Mitsunobu reaction in glycoside synthesis: a) G. Grynkiewicz, Carbohydr. Res. 1977, 53, c11-c12; b) P. J. Garegg, T. Iversen, T. Norberg, Carbohydr. Res. 1979, 73, 313-314; c) K. Åkerfeldt, P. J. Garegg, T. Iversen, Acta Chem. Scand. B 1979, 33, 467-468; d) T. Kometani, H. Kondo, Y. Fujimori, Synthesis 1988, 1005-1007; e) G. T. Badman, D. V. S. Green, M. Voyle, J. Organomet. Chem. 1990, 388, 117-121; f) W. R. Roush, X.-F. Lin, J. Org. Chem. 1991, 56, 5740-5742; g) A. Lubineau, E. Meyer, P. Place, Carbohydr. Res. 1992, 228, 191-203; h) A. Bouali, G. Descotes, D. F. Ewing, A. Grouiller, J. Lefkidou, A.-D. Lespinasse, G. Mackenzie, J. Carbohydr. Chem. 1992, 11, 159-169; i) W. R. Roush, X.-F. Lin, J. Am. Chem. Soc. 1995, 117, 2236-2250.
54. Although commercially available (Aldrich), compound 2 was conveniently prepared from D-mannose in multigram scale according to: O. T. Schmidt, Methods Carbohydr. Chem. 1963, 2, 318-325.
55. S. Shinkai, K. Araki, P. D. J. Grootenhuis, D. N. Reinhoudt, J. Chem. Soc. Perkin Trans. 2 1991, 1883-1886.
56. 1, 2 ≈0 Hz, see: J. D. Stevens, H. G. Fletcher, J. Org. Chem. 1968, 33, 1799-1805. A similar trend has been observed for 2,3:5,6-di-O-isopropylidene-D-mannofuranoside derivatives, see: a) H. Ohrui, G. H. Jones, J. G. Moffatt, M. L. Maddox, A. T. Christensen, S. K. Byram, J. Am. Chem. Soc. 1975, 97, 4602-4613; b) M. Valpuesta, P. Durante, F. J. López-Herrera, Tetrahedron 1993, 49, 9547-9560.
57. 1, 2 ≈0 Hz, see: J. D. Stevens, H. G. Fletcher, J. Org. Chem. 1968, 33, 1799-1805. A similar trend has been observed for 2,3:5,6-di-O-isopropylidene-D-mannofuranoside derivatives, see: a) H. Ohrui, G. H. Jones, J. G. Moffatt, M. L. Maddox, A. T. Christensen, S. K. Byram, J. Am. Chem. Soc. 1975, 97, 4602-4613; b) M. Valpuesta, P. Durante, F. J. López-Herrera, Tetrahedron 1993, 49, 9547-9560.
58. 1, 2 ≈0 Hz, see: J. D. Stevens, H. G. Fletcher, J. Org. Chem. 1968, 33, 1799-1805. A similar trend has been observed for 2,3:5,6-di-O-isopropylidene-D-mannofuranoside derivatives, see: a) H. Ohrui, G. H. Jones, J. G. Moffatt, M. L. Maddox, A. T. Christensen, S. K. Byram, J. Am. Chem. Soc. 1975, 97, 4602-4613; b) M. Valpuesta, P. Durante, F. J. López-Herrera, Tetrahedron 1993, 49, 9547-9560.
59. Calix[4]arenes having a cone conformation show the signals for the equatorial and axial protons of the methylene bridges as well resolved doublets at δ≈3 and 4, respectively. See: a) ref. [1a], pp. 108-111; b) M. Iqbal, T. Mangiafico, C. D. Gutsche, Tetrahedron 1987, 43, 4917-4930; c) A. Casnati, A. Arduini, E. Ghidini, A. Pochini, R. Ungaro, ibid. 1991, 47, 2221-2228.
60. Calix[4]arenes having a cone conformation show the signals for the equatorial and axial protons of the methylene bridges as well resolved doublets at δ≈3 and 4, respectively. See: a) ref. [1a], pp. 108-111; b) M. Iqbal, T. Mangiafico, C. D. Gutsche, Tetrahedron 1987, 43, 4917-4930; c) A. Casnati, A. Arduini, E. Ghidini, A. Pochini, R. Ungaro, ibid. 1991, 47, 2221-2228.
61. Calix[4]arenes having a cone conformation show the signals for the equatorial and axial protons of the methylene bridges as well resolved doublets at δ≈3 and 4, respectively. See: a) ref. [1a], pp. 108-111; b) M. Iqbal, T. Mangiafico, C. D. Gutsche, Tetrahedron 1987, 43, 4917-4930; c) A. Casnati, A. Arduini, E. Ghidini, A. Pochini, R. Ungaro, ibid. 1991, 47, 2221-2228.
62. The signals for the carbon atoms of the methylene groups connecting two adjacent phenyl moieties in a syn orientation (e.g. in the cone conformation) appear at δ≈31. See: C. Jaime, J. de Mendoza, P. Prados, P.M. Nieto, C. Sánchez, J. Org. Chem. 1991, 56, 3372-3376.
63. 6]DMSO. For a discussion on the conformations of calix[4]arenes partially alkylated at the lower rim, see: L. C. Grenen, E. Steinwender, B. T. G. Lutz, J. H. van der Maas, D. N. Reinhoudt, J. Chem. Soc. Perkin Trans. 2 1992, 1893-1898.
64. Compound 5 was prepared according to: G. Excoffier, D. Gagnaire, J.-P. Utille, Carbohydr. Res. 1975, 39, 368-373.
65. 5, 6b = 4.5 Hz; H-5).
66. -1 from a 25 x 100 mm silica gel column (60 Å, 6 μm) with 82:18 cyclohexane: AcOEt (detection at 280 nm).
67. 6 showed a constant α/β ratio of 3:1 even in the presence of calixarene 1a.
68. N1-type reaction, see refs. [16] and [17h].
69. J.-D. van Loon, A. Arduini, L. Coppi, W Verboom, A. Pochini, R. Ungaro, S. Harkema, D. N. Remhoudt, J. Org. Chem. 1990, 55, 5639-5646.
70. A. Casnati, M. Fochi, P. Minari, A. Pochini, M. Reggiani, R. Ungaro, D. N. Reinhoudt, Gazz. Chim. Ital. 1996, 126, 99-106.
71. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
72. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
73. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
74. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
75. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
76. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
77. For reviews on glycosylation reactions, see: a) H. Paulsen, Angew. Chem. 1982, 94, 184-253; Angew. Chem. Int. Ed. Engl. 1982, 21, 155-224; b) R. R. Schmidt, ibid. 1986, 98, 213-236 and 1986, 25, 212-235; c) K. Toshima, K. Tatsuta, Chem. Rev. 1993, 93, 1503-1531; d) G.-J. Boons, Tetrahedron 1996, 52, 1095-1121; e) G.-J. Boons, Contemp. Org. Synth. 1996, 3, 173-200.
78. For short reviews on thioglycosides, see: a) P. Fügedi, P. J. Garegg, H. Löhn, T. Norberg, Glycoconjugate J. 1987, 4, 97-108; b) P. Sinaÿ, Pure Appl. Chem. 1991, 63, 519-528.
79. For short reviews on thioglycosides, see: a) P. Fügedi, P. J. Garegg, H. Löhn, T. Norberg, Glycoconjugate J. 1987, 4, 97-108; b) P. Sinaÿ, Pure Appl. Chem. 1991, 63, 519-528.
80. a) P. J. Garegg, P. Konradsson, I. Kvarnström, T. Norberg, S. C. T. Svensson, B. Wigilius, Acta Chem. Scand. B 1985, 39, 569-577;
81. b) F. Dasgupta, P. J. Garegg, Carbohydr. Res. 1988, 177, c13-c17;
82. c) A. Marra, J.-M. Mallet, C. Amatore, P. Sinaÿ, Synlett 1990, 572-575;
83. d) Y. Ito, T. Ogawa, M. Numata, M. Sugimoto, Carbohydr. Res. 1990, 202, 165-175;
84. e) J.-M. Mallet, G. Meyer, F. Yvelin, A. Jutand, C. Amatore, P. Sinaÿ, Carbohydr. Res. 1993, 244, 237-246.
85. The activation of thiobenzothiazolyl glycosides and glycosyl xanthates by copper(II) triflate has been reported, see: a) T. Mukaiyama, T. Nakatsuka, S. Shoda, Chem. Lett. 1979, 487-490; b) A. Marra, L. K. Shi Shun, F. Gauffeny, P. Sinaÿ, Synlett 1990, 445-448; A. Marra, F. Gauffeny, P. Sinaÿ, Tetrahedron 1991, 47, 5149-5160.
86. The activation of thiobenzothiazolyl glycosides and glycosyl xanthates by copper(II) triflate has been reported, see: a) T. Mukaiyama, T. Nakatsuka, S. Shoda, Chem. Lett. 1979, 487-490; b) A. Marra, L. K. Shi Shun, F. Gauffeny, P. Sinaÿ, Synlett 1990, 445-448; A. Marra, F. Gauffeny, P. Sinaÿ, Tetrahedron 1991, 47, 5149-5160.
87. The activation of thiobenzothiazolyl glycosides and glycosyl xanthates by copper(II) triflate has been reported, see: a) T. Mukaiyama, T. Nakatsuka, S. Shoda, Chem. Lett. 1979, 487-490; b) A. Marra, L. K. Shi Shun, F. Gauffeny, P. Sinaÿ, Synlett 1990, 445-448; A. Marra, F. Gauffeny, P. Sinaÿ, Tetrahedron 1991, 47, 5149-5160.
88. 1, 2 =7.4-7.7 Hz, see Experimental Section).
89. A. Arduini, S. Fanni, A. Pochini, A. R. Sicuri, R. Ungaro, Tetrahedron 1995, 51, 7951-7958.
90. 2O decreases greatly.
91. 1H NMR experiments were performed at 300 K by adding a 0.096 M solution of the guest to a 0.01 M solution of the host (host-guest ratio from 2:1 to 1:9).
92. T. H. Webb, C. S. Wilcox, Chem. Soc Rev. 1993, 383-395.
93. The following compounds were examined: D-and L-phenylglycine, N-acetyl-L-alanyl-L-alanine, guanosine 5′-monophospate disodium salt, D-and L-arabinose, phenyl 1-thio-β-D-glucopyranoside, p-nitrophenyl β-D-glucopyranoside, N-acetyl-D-glucosamine. N-acetylneuraminic acid.
94. -4, see D. M. Rudkevich, W Verboom, D. N. Reinhoudt, J. Org. Chem. 1994, 59, 3683-3686.
95. G. Das, A. D. Hamilton, J. Am. Chem. Soc. 1994, 116, 11 139-11 140.
96. a) J.-M. Neumann, M. Hervé, J.-C. Debouzy, F. I. Guerra, C. Gouyette, B. Dupraz, T. Huynh-Dinh, J. Am. Chem. Soc. 1989, 111, 4270-4277;
97. b) H. Yuasa, M. M. Palcic, O. Hindsgaul, Can. J. Chem. 1995, 73, 2190-2195.
98. D. D. Perrin, W. L. F. Armarego, Purification of Laboratory Chemicals, 3rd ed., Pergamon Press, Oxford, 1988.
99. W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
100. a) V. Böhmer, K. Jung, M. Schön, A. Wolff, J. Org. Chem. 1992, 57, 790-792;
101. b) C. D. Gutsche, K. A. See, ibid. 1992, 57, 4527-4539.
102. Z. Pakulsky, D. Pierozynski, A. Zamojsky Tetrahedron 1994, 50, 2975-2992.
103. E. Kallin, H. Lönn, T. Norberg, J. Carbohydr. Chem. 1990, 9, 721-733.
104. A. Ikeda, T. Nagasaki, K. Araki, S. Shinkai, Tetrahedron 1992, 48, 1059-1070.
105. Note added in proof: While this manuscript was in press, we achieved the synthesis of calixsugars wherein the sugar units are linked to the macrocycle by a carbon-carbon bond (A. Dondoni, M. Kleban, A. Marra, Tetrahedron Lett. 1997, 38, 7801-7804.