Calixsugars: Preparation of upper rim O-ketopyranosyl calix[4]arenes

Journal of Organic Chemistry

Volumn 61, Issue 15, 1996, Pages 5155-5158

  Marra, Alberto ^a   Dondoni, Alessandro ^a   Sansone, Francesco ^a,b  

^a UNIVERSITY OF FERRARA   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; CARBOHYDRATE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030017406     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960417g     Document Type: Article

References (39)

1. (a) Gutsche, C. D. In Calixarenes, Monograph in Supramolecular Chemistry, Vol. 1; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, 1989.
2. (b) Calixarenes, a Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
3. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
4. For recent reviews, see: (a) Takeshita, M.; Shinkai, S. Bull. Chem. Soc. Jpn. 1995, 68, 1088. (b) Gutsche, C. D. Aldrichimica Acta 1995, 28, 3. (c) Lhoták, P.; Shinkai, S. J. Synth. Org. Chem., Jpn. 1995, 53, 963.
5. For recent reviews, see: (a) Takeshita, M.; Shinkai, S. Bull. Chem. Soc. Jpn. 1995, 68, 1088. (b) Gutsche, C. D. Aldrichimica Acta 1995, 28, 3. (c) Lhoták, P.; Shinkai, S. J. Synth. Org. Chem., Jpn. 1995, 53, 963.
6. For recent reviews, see: (a) Takeshita, M.; Shinkai, S. Bull. Chem. Soc. Jpn. 1995, 68, 1088. (b) Gutsche, C. D. Aldrichimica Acta 1995, 28, 3. (c) Lhoták, P.; Shinkai, S. J. Synth. Org. Chem., Jpn. 1995, 53, 963.
7. Gutsche, C. D.; Iqbal, M. Org. Synth. 1990, 68, 234.
8. Unmodified calix[4]arenes are conformationally mobile macrocycles which adopt a cone conformation because of strong hydrogen bonds among the hydroxy groups. The n-propylation of these groups inhibits the oxygen-through-the-annulus rotation and allows the isolation of the blocked cone conformational isomer (see: (a) Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Chem. Lett. 1989, 1747. (b) Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4955).
9. Unmodified calix[4]arenes are conformationally mobile macrocycles which adopt a cone conformation because of strong hydrogen bonds among the hydroxy groups. The n-propylation of these groups inhibits the oxygen-through-the-annulus rotation and allows the isolation of the blocked cone conformational isomer (see: (a) Araki, K.; Iwamoto, K.; Shinkai, S.; Matsuda, T. Chem. Lett. 1989, 1747. (b) Iwamoto, K.; Araki, K.; Shinkai, S. J. Org. Chem. 1991, 56, 4955).
10. Besides the crown ether moieties, also porphyrin (Nagasaki, T.; Fujishima, H.; Shinkai, S. Chem. Lett. 1994, 989) and β-cyclodextrin (D' Alessandro, F.; Gulino, F. G.; Impellizzeri, G.; Pappalardo, G.; Rizzarelli, E.; Sciotto, D.; Vecchio, G. Tetrahedron Lett. 1994, 35, 629. van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1151) have been covalently linked to calix[4]arenes.
11. Besides the crown ether moieties, also porphyrin (Nagasaki, T.; Fujishima, H.; Shinkai, S. Chem. Lett. 1994, 989) and β-cyclodextrin (D' Alessandro, F.; Gulino, F. G.; Impellizzeri, G.; Pappalardo, G.; Rizzarelli, E.; Sciotto, D.; Vecchio, G. Tetrahedron Lett. 1994, 35, 629. van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1151) have been covalently linked to calix[4]arenes.
12. Besides the crown ether moieties, also porphyrin (Nagasaki, T.; Fujishima, H.; Shinkai, S. Chem. Lett. 1994, 989) and β-cyclodextrin (D' Alessandro, F.; Gulino, F. G.; Impellizzeri, G.; Pappalardo, G.; Rizzarelli, E.; Sciotto, D.; Vecchio, G. Tetrahedron Lett. 1994, 35, 629. van Dienst, E.; Snellink, B. H. M.; von Piekartz, I.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1995, 1151) have been covalently linked to calix[4]arenes.
13. Marra, A.; Scherrmann, M.-C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R. Angew. Chem., Int. Ed. Engl. 1994, 33, 2479.
14. Dondoni, A.; Scherrmann, M.-C. J. Org. Chem. 1994, 59, 6404.
15. Dondoni, A.; Marra, A.; Rojo, I.; Scherrmann, M.-C. Tetrahedron 1996, 52, 3057.
16. Dondoni, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992, pp 377-437. Dondoni, A. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, and VCH: Weinheim, 1992; pp 105-128.
17. Dondoni, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992, pp 377-437. Dondoni, A. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, and VCH: Weinheim, 1992; pp 105-128.
18. This feature favors the use of thiazole instead of furan since the cleavage of the furan ring to carboxyl group requires strong oxidative conditions which are not tolerated by the above protective groups (Dondoni, A.; Marra, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323 and references cited therein). However, due to the electron-donor character of the furan ring, the glycosylation reaction should be favored by the presence of this heterocycle at the anomeric position (see: (a) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929).
19. This feature favors the use of thiazole instead of furan since the cleavage of the furan ring to carboxyl group requires strong oxidative conditions which are not tolerated by the above protective groups (Dondoni, A.; Marra, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323 and references cited therein). However, due to the electron-donor character of the furan ring, the glycosylation reaction should be favored by the presence of this heterocycle at the anomeric position (see: (a) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929).
20. This feature favors the use of thiazole instead of furan since the cleavage of the furan ring to carboxyl group requires strong oxidative conditions which are not tolerated by the above protective groups (Dondoni, A.; Marra, A.; Scherrmann, M.-C. Tetrahedron Lett. 1993, 34, 7323 and references cited therein). However, due to the electron-donor character of the furan ring, the glycosylation reaction should be favored by the presence of this heterocycle at the anomeric position (see: (a) Danishefsky, S. J.; Pearson, W. H.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 1280. (b) Danishefsky, S. J.; DeNinno, M. P.; Chen, S. J. Am. Chem. Soc. 1988, 110, 3929).
21. 2). For recent articles, see: (a) Lönn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115. (b) Müller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. (c) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. (d) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 5657.
22. 2). For recent articles, see: (a) Lönn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115. (b) Müller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. (c) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. (d) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 5657.
23. 2). For recent articles, see: (a) Lönn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115. (b) Müller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. (c) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. (d) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 5657.
24. 2). For recent articles, see: (a) Lönn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115. (b) Müller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763. (c) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H. J. Org. Chem. 1994, 59, 864. (d) Heskamp, B. M.; Veeneman, G. H.; van der Marel, G. A.; van Boeckel, C. A. A.; van Boom, J. H. Tetrahedron 1995, 51, 5657.
25. Dondoni, A.; Scherrmann, M.-C.; Marra, A.; Delépine, J.-L. J. Org. Chem. 1994, 59, 7517.
26. Casnati, A.; Fochi, M.; Minari, P.; Pochini, A.; Reggiani, M.; Ungaro, R.; Reinhoudt, D. N. Gazz. Chim. Ital. 1996, 126, 99.
27. Also isolated was unreacted thiazolyl ketol acetate 1 in 32% yield.
28. Calix[4]arenes having a cone conformation display the signals for the equatorial and axial protons of the methylene bridges as well resolved doublets at δ ∼3 and δ ∼4, respectively (see ref 1a, pp 108-111).
29. Babirad, S. A.; Wang, Y.; Kishi, Y. J. Org. Chem. 1987, 52, 1370.
30. Dondoni, A.; Marra, A.; Perrone, D. J. Org. Chem. 1993, 58, 275.
31. Yamada, S.; Morizono, D.; Yamamoto, K. Tetrahedron Lett. 1992, 33, 4329.
32. (a) Haverkamp, J.; Spoormaker, T.; Dorland, L.; Vliegenthart, J. F. G.; Schauer, R. J. Am. Chem. Soc. 1979, 101, 4851.
33. (b) Hori, H.; Nakajima, T. Nishida, Y.; Ohrui, H.; Meguro, H. Tetrahedron Lett. 1988, 29, 6317.
34. (c) Prytulla, S.; Lauterwein, J.; Klessinger, M.; Thiem, J. Carbohydr. Res. 1991, 215, 345.
35. C-1,H-3 ≈ 4.0 Hz).
36. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988.
37. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
38. The issue regarding these discrepancies in elemental analyses has been addressed by authoritative researchers in calixarene chemistry. See: (a) Böhmer, V.; Jung, K.; Schön, M.; Wolff, A. J. Org. Chem. 1992, 57, 790. (b) Gutsche, C. D.; See, K. A. J. Org. Chem. 1982, 57, 4527.
39. The issue regarding these discrepancies in elemental analyses has been addressed by authoritative researchers in calixarene chemistry. See: (a) Böhmer, V.; Jung, K.; Schön, M.; Wolff, A. J. Org. Chem. 1992, 57, 790. (b) Gutsche, C. D.; See, K. A. J. Org. Chem. 1982, 57, 4527.