Efficient monomodification of the secondary hydroxy groups of β- cyclodextrin

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 332-333

  Chiu, Sheng Hsien ^a   Myles, David C ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

BETA CYCLODEXTRIN;

ACYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL MODIFICATION; ISOMER; METHYLATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033593392     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981866e     Document Type: Article

References (31)

1. (a) Motesharei, K.; Myles, D. C. J. Am. Chem. Soc. 1994, 116, 7413.
2. (b) Motesharei, K.; Myles, D. C. J. Am. Chem. Soc. 1997, 119, 6674.
3. (c) Horton, R. C.; Myles, D. C. J. Am. Chem. Soc. 1997, 119, 12980.
4. (a) Bender, M. L.; Komiyama, M. Cyclodextrin Chemistry; Springer. Berlin. 1978.
5. (b) Breslow, R. Pure Appl. Chem. 1994, 66, 1573.
6. (c) D'Souza, V. T.; Bender, M. L. Acc. Chem. Res. 1987, 20, 146.
7. (a) Szejtli, J. Cyclodextrin Technology. In Topics in Inclusion Science; Davies, J. E. D., Ed.; Kluwer: Dordrecht, 1988.
8. (b) Pfannemuller, B.; Burchard, W. Makromol. Chem. 1969, 121, 1.
9. Ye, H.; Tong, W.; D'Souza, V. T. J. Am. Chem. Soc. 1992, 114, 5470.
10. (a) Ohvo, H.; Slotte, J. P. Biochemistry 1996, 35, 8108.
11. (b) Anderson, T.; Sundahl, M.; Westman, G.; Wennerstorm, O. Tetrahedron Lett. 1994, 35, 7103.
12. (a) Rojas, M. T.; Koniger, R.; Stoddart, J. F.; Kaifer, A. E. J. Am. Chem. Soc. 1995, 117, 336.
13. (b) Lahav, M.; Ranjit, K. T.; Katz, E.; Willner, I. Chem. Commun. 1997, 259.
14. (c) Odashima, K.; Kotato, M.; Sugawara, M.; Umezawa, Y. Anal. Chem. 1993, 65, 927.
15. (a) Ueno, A.; Breslow, R. Tetrahedron Lett. 1982, 23, 3451.
16. (b) Tian, S.; Forgo, P.; D'Souza, V. T. Tetrahedron Lett. 1996, 37, 8309.
17. (c) Rong, D.; D'Souza, V. T. Tetrahedron Lett. 1990, 30, 4275.
18. (d) Martin, K. A.; Mortellaro, M. A.; Sweger, R. W.; Fikers, L. E.; Winn, D. T.; Clary, S.; Johnson, M. P.; Czarnik, A. W. J. Am. Chem. Soc. 1995, 117, 10443.
19. (e) Khan, A. R.; Forgo, P.; Stine, K. J.; D'souza, V. T. Chem. Rev. 1998, 98, 1977.
20. Fugedi, P. Carbohydr. Res. 1995, 192, 366.
21. Compound 2 can be directly generated by treating β-cyclodextrin itself with 15 equiv of TBSCl in pyridine for 48 h. If β-cyclodextrin is treated with only 7.7 equiv of TBSCl for 24 h, only compound 1 is formed. In contrast to many β-cyclodextrin derivatives, compound 1 is easily handled and purified with normal-phase chromatography.
22. (a) Czarniecki, M. F.; Breslow, R. J. Am. Chem. Soc. 1978, 7771.
23. (b) Vanetten, R. L.; Clowes, G. A.; Sebastian, J. F.; Bender, M. L. J. Am. Chem. Soc. 1967, 7771.
24. (c) Kurono, Y.; Stamoudis, V.; Bender, M. L. Bioorg. Chem. 1976, 5, 393.
25. (a) Khan, A. R.; Barton, L.; D'Souza, V. T.J. Org. Chem. 1996, 61, 8301.
26. (b) Fugita, K.; Nagamura, S.; Tahara, T.; Kogas, T. J. Am. Chem. Soc. 1985, 107, 3233.
27. Icheln, D.; Gehrcke, B.; Piprek, Y.; Mischnick, P.; Konig, W. A.; Dessoy, M. A.; Morel, A. F. Carbohydr. Res. 1996, 280, 237.
28. Mischnick, P.; Lange, M.; Gohdes, M.; Stein, A.; Petzold, K. Carbohydr. Res. 1995, 277, 179.
29. (a) Fugita, K.; Yamamura, H.; Imoto, T.; Tabushi, I.; Sanzo, H.; Maidashi, H. Chem. Lett. 1988, 543.
30. (b) Gadelle, A.; Defaye, J. Angew. Chem., Int. Ed. Engl. 1991, 30, 78.
31. (c) Alker, D.; Aston, P. R.; Harding, V. D.; Koniger, R.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Tetrahedron Lett. 1994, 35, 9091.