Synthesis of per(5-carboxy-5-dehydroxymethyl)-α- and β-cyclodextrins - Self-assembly of the per(2,3-di-O-methyl)-protected homologues into highly stable dimers, driven by multiple hydrogen bonds

European Journal of Organic Chemistry

Volumn , Issue 18, 2000, Pages 3133-3137

  Kraus, Tomáš ^a   Buděšínský, Miloš ^a   Závada, Jiří ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Carboxylic acids; Cyclodextrins; Self assembly; Supramolecular chemistry

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CARBON; CARBOXYLIC ACID DERIVATIVE; CYCLODEXTRIN DERIVATIVE; DIMER; HYDROGEN; PER(5 CARBOXY 5 DEHYDROXYMETHYL)ALPHA CYCLODEXTRIN; PER(5 CARBOXY 5 DEHYDROXYMETHYL)BETA CYCLODEXTRIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL BINDING; HYDROGEN BOND; HYDROLYSIS; OXIDATION; PRESSURE; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTITATIVE ASSAY; SYNTHESIS; VAPOR;

EID: 0342409286     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200009)2000:18<3133::AID-EJOC3133>3.0.CO;2-P     Document Type: Article

References (31)

1. [1a] J. Szejtli, Cyclodextrins and Their Inclusion Complexes, Akademiai kiado. Budapest, 1982.
2. [1b] M. L. Bender, M. Komiyama, Cyclodextrin Chemistry, Springer Verlag, Berlin, 1978.
3. [1c] G. Le Bas, N. Rysanek, Cyclodextrins and Their Industrial Uses, (Ed.: D. Duchene), Editions de Sante, Paris, 1987.
4. [1d] Comprehensive Supramolecular Chemistry, (Eds.: J. L. Atwood, J.-M. Lehn), Vol. 3, Cyclodextrins, (Eds.: J. Szejtli, T. Osa). Pergamon, Oxford, U.K., 1996.
5. [2a] A. P. Croft, R. A. Bartsch, Tetrahedron 1983, 39, 1417-1474.
6. [2b] A. R. Khan, P. Forgo, K. J. Stine, V. T. D'Souza, Chem. Rev. 1998, 98, 1977-1996.
7. [2c] B. I. Gorin, R. J. Riopelle, G. R. J. Thatcher, Tetrahedron Lett. 1996, 37, 4647-4650.
8. [2d] P. R. Ashton, R. Koniger, J. F. Stoddart, J. Org. Chem 1996, 61, 903-908.
9. [2e] D. Gadelle, J. Defaye, Angew. Chem. Int. Ed. Engl. 1991, 30, 78.
10. [3a] A. J. Lewis, S. Bernstein, US Patent 4,247,535, 1981.
11. [3b] B. Casu, G. Scovenna, A. J. Cifonelli, A. S. Perlin, Carbohydr. Res. 1978, 63, 13-27.
12. [3c] F. Guillo, B. Hamelin, L. Jullien, J. Cancelli, J.-M. Lehn, L. De Robertis, H. Driguez, Bull. Soc. Chim. Fr. 1995, 132, 857-866.
13. [3d] P. S. Chang, J. F. Robyt, Carbohydr. Lett. 1998, 3, 31-38.
14. [3e] K. Schnatbaum, H. J. Schafer, Synthesis 1999, 864-872.
15. [4a] P. Holý, J Závada, J. Podlaha, I. Císařová, Angew: Chem. Int. Ed. 1999, 38, 381-383.
16. [4b] M. Tichý, T. Kraus, J. Závada, I. Císařová, J. Podlaha, Tetrahedron: Asymmetry 1999, 10, 3277-3280.
17. A. R. Khan, P. Forgo, K. J. Stine, V. T. D'Souza, Chem. Rev. 1998, 98, p. 1986.
18. J. Boger, R. J. Corcoran, J.-M. Lehn, Helv. Chim. Acta 1978, 61, pp. 2192-2193.
19. [7a] K. Takeo, K. Uemura, H. Mitoh, J. Carbohydr. Chem. 1988, 7, 293-308.
20. [7b] K. Takeo, H. Mitoh, K. Uemura. Carbahydr. Res 1989, 187, 203-221.
21. [7c] P. Fugedi, Carbohydr. Res 1989, 192, 366-369
22. [8a] L. Kaichang, R. F. Helm, Carbohydr. Res. 1995, 273, 249-253.
23. [8b] S. J. H. F. Arts, E. J. M. Mombarg, H. van Bekkum, R. A. Sheldon, Synthesis 1997, 597-613.
24. [8c] A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Carbohydr. Res. 1995, 269, 89-98 and references given therein.
25. [9a] A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Synthesis 1996, 1153-1174.
26. [9b] N. J. Davis, S. L. Flitsch. Tetrahedron Lett. 1993, 34, 1181-1184.
27. P. L. Anelli, C. Biffi, F. Montanari, S. Quici, J. Org. Chem. 1987, 52, 2559-2562.
28. [11a] A. E. J. de Nooy, A. C. Besemer, H. van Bekkum, Tetrahedron 1995, 51, 8023-8032.
29. [11b] K. L. Reddy, K. B. Sharpless. J. Am. Chew. Soc. 1998, 120, 1207-1217.
30. [3e]
31. In the course of the reaction of the protected homologues 1a, 1b and 3a, 3b, the oxidation reagents could be detected throughout the whole reaction time.