Regiospecific synthesis of 2(A),2(B)-disulfonated γ-cyclodextrin

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 933-936

  Teranishi, Katsunori ^a   Hisamatsu, Makoto ^a   Yamada, Tetsuya ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

cyclodextrin; Disulfonation; Regiospecificity

Indexed keywords

CYCLODEXTRIN DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034606919     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02193-0     Document Type: Article

References (30)

1. For a review, see: Breslow, R.; Dong, S. D. Chem. Rev. 1998, 98, 1997-2011.
2. (a) Ueno, A.; Takahashi, K.; Osa, T. J. Chem. Soc., Chem. Commun. 1980, 921-922.
3. (b) Ueno, A.; Takahashi, K.; Hino, Y.; Osa, T. J. Chem. Soc., Chem. Commun. 1981, 194-195.
4. (c) Emert, J.; Kodali, D.; Catena, R. J. Chem. Soc., Chem. Commun. 1981, 758-759.
5. (d) Kobayashi, N.; Hino, Y.; Ueno, A.; Osa, T. Bull. Chem. Soc. Jpn. 1983, 56, 1849-1850.
6. (e) Ueno, A.; Tomita, Y.; Osa, T. J. Chem. Soc., Chem. Commun. 1983, 976-977.
7. (f) Ueno, A.; Tomita, Y.; Osa, T. Chem. Lett. 1983, 1635-1638.
8. (g) Ueno, A.; Moriwaki, F.; Osa, T.; Ikeda, T.; Toda, F.; Hattori, K. Bull. Chem. Soc. Jpn. 1986, 59, 3109-3112.
9. (h) Ueno, A.; Moriwaki, F.; Osa, T.; Hamada, F.; Murai, K. J. Am. Chem. Soc. 1988, 110, 4323-4328.
10. Teranishi, K.; Tanabe, S.; Komoda, A.; Hisamatsu, M.; Yamada, T.; 1998, 9th International Symposium on Cyclodextrins, 2-P-36.
11. For a review, see: Khan, A. F.; Forgo, P.; Stine, K. J.; D'Souza, V. T. Chem. Rev. 1998, 98, 1977-1996.
12. (a) Ueno, A.; Moriwaki, F.; Osa, T.; Hamada, F.; Murai, K. Tetrahedron Lett. 1985, 26, 3339-3342.
13. (b) Ueno, A.; Moriwaki, F.; Osa, T.; Hamada, F.; Murai, K. Bull. Chem. Soc. Jpn. 1986, 59, 465-470.
14. (c) Fujita, K.; Yamamura, H.; Imoto, T.; Fujioka, T.; Mihashi, K. J. Org. Chem. 1988, 53, 1943-1947.
15. (d) Hamada, F.; Fukushima, M.; Osa, T.; Ikeda, T.; Toda, F.; Ueno, A. Makromol. Chem., Rapid Commun. 1993, 14, 287-291.
16. (a) Wang, Y.; Ikeda, T.; Ueno, A.; Toda, F. Chem. Lett. 1992, 863-866.
17. (b) Takahashi, K.; Hattori, K. J. Inclusion Phenom. 1984, 2, 661-667.
18. (a) Murakami, T.; Harata, K.; Morimoto, S. Tetrahedron Lett. 1987, 28, 321-324.
19. (b) Teranishi, K.; Tanabe, S.; Hisamatsu, M.; Yamada, T. Biosci., Biotechnol., Biochem. 1998, 62, 1249-1252.
20. (a) Fujita, K.; Nagamura, S.; Imoto, T.; Tahara, T.; Koga, T. J. Am. Chem. Soc. 1985, 107, 3233-3235.
21. (b) Fujita, K.; Ishizu, T.; Oshiro, K.; Obe, K. Bull. Chem. Soc. Jpn. 1989, 62, 2960-2962.
22. Teranishi, K.; Watanabe, K.; Hisamatsu, M.; Yamada, T. J. Carbohydr. Chem. 1998, 17, 489-494.
23. Tabushi, I.; Kuroda, Y.; Yokota, K.; Yuan, L.C. J. Am. Chem. Soc. 1981, 103, 711-712.
24. For a review in structural studies of cyclodextrins, see: Harata, K. Chem. Rev. 1998, 98, 1803-1827.
25. Work, J. L.; Herweh, J. E. J. Polym. Sci., A-1 1968, 2022-2030.
26. Berlin, Y. A.; Chakhmakhcheva, O. G.; Efimov, V. A.; Kolosov, M. N.; Korobko, V. G. Tetrahedron Lett. 1973, 1353-1354.
27. The NMR properties and reactions of 2-O-tosyl and manno-epoxido cyclodextrins were reported in the following papers: (a) Ueno, A.; Breslow, R. Tetrahedron Lett. 1982, 23, 3451-3454.
28. (b) Breslow, R.; Czarnik, A. W. J. Am. Chem. Soc. 1983, 105, 1390-1391. For di-manno-epoxido α, and β-cyclodextrins, see Ref. 8.
29. For a review in NMR studies of cyclodextrins, see: Schneider, H.; Hacket, F.; Rudiger, V.; Ikeda, H. Chem. Rev. 1998, 98, 1755-1785.
30. B-dideoxy α-cyclodextrin was reported in the following paper: Fujita, K.; Egashira, Y.; Imoto, T.; Fujioka, T.; Mihashi, K.; Tahara, T.; Koga, T. Chem. Lett. 1989, 429-432.