Hetero-bifunctionalization of the secondary face of β-cyclodextrin: selective 3G-sulfonylation and subsequent 2G,3G-epoxidation of 3A-azido-3A-deoxy-altro-β-cyclodextrin

Tetrahedron Letters

Volumn 47, Issue 37, 2006, Pages 6599-6602

  Fukudome, Makoto ^a   Matsushima, Aya ^a   Yuan, De Qi ^a   Fujita, Kahee ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Altrose; Azide; Cyclodextrin; Epoxide; Modification; Sulfonylation

Indexed keywords

ALKALI; AZIDE; BETA CYCLODEXTRIN DERIVATIVE; EPOXIDE; GLUCOSIDE; HYDROXYL GROUP; NAPHTHALENESULFONIC ACID DERIVATIVE; SUGAR; SULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; EPOXIDATION; SYNTHESIS;

EID: 33746837222     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.028     Document Type: Article

References (26)

1. Motherwell W.B., Bingham M.J., and Six Y. Tetrahedron 57 (2001) 4663-4686
2. Breslow R., and Dong S.D. Chem. Rev. 98 (1998) 1997-2011
3. Hedges A.R. Chem. Rev. 98 (1998) 2035-2044
4. Uekama K., Hirayama F., and Irie T. Chem. Rev. 98 (1998) 2045-2076
5. For a recent review on the modification of CDs, see:. Kahn A.R., Forgo P., Stine K.J., and D'Souza V.T. Chem. Rev. 98 (1998) 1977-1996
6. Fujita K., Yamamura H., Egashira Y., and Imoto T. Tetrahedron Lett. 33 (1992) 3511-3514
7. Fujita K., Yamamura H., and Imoto T. Tetrahedron Lett. 32 (1991) 6737-6740
8. Fasella E., Dong S.D., and Breslow R. Bioorg. Med. Chem. 7 (1999) 709
9. Tabushi I., Kuroda Y., Yamada M., Higashimura H., and Breslow R. J. Am. Chem. Soc. 107 (1985) 5545-5546
10. Yuan D.-Q., Yamada T., and Fujita K. Chem. Commun. (2001) 2706-2707
11. Fukudome M., Sugimoto Y., Yuan D.-Q., and Fujita K. Chem. Commun. (2005) 3168-3170
12. Fujita K., Ohta K., Ikegami Y., Shimada H., Tahara T., Nogami Y., Koga T., Saito K., and Nakajima T. Tetrahedron Lett. 35 (1994) 9577-9580
13. Angyal S.J. Aust. J. Chem. 21 (1968) 2737-2746
14. Dowd M.K., French A.D., and Reilly P.J. Carbohydr. Res. 264 (1994) 1-19
15. Lichtenthaler F.W., and Mondel S. Carbohydr. Res. 303 (1997) 293-302
16. Fujita K., Chen W.-H., Yuan D.-Q., Nogami Y., Koga T., Fujioka T., Mihashi K., Immel S., and Lichtenthaler F.W. Tetrahedron: Asymmetry 10 (1999) 1689-1696
17. Chen W.-H., Fukudome M., Yuan D.-Q., Fujioka T., Mihashi K., and Fujita K. Chem. Commun. (2000) 541-542
18. Lindner H.J., Yuan D.-Q., Fujita K., Kubo K., and Lichtenthaler F.W. Chem. Commun. (2003) 1730-1731
19. Yuan D.-Q., Tahara T., Chen W.-H., Okabe Y., Yang C., Yagi Y., Nogami Y., Fukudome M., and Fujita K. J. Org. Chem. 68 (2003) 9456-9466
20. Fukudome M., Fujioka T., Yuan D.-Q., and Fujita K. Tetrahedron Lett. 42 (2001) 293-295
21. Fukudome M., Yuan D.-Q., and Fujita K. Tetrahedron Lett. 46 (2005) 1115-1118
22. Fukudome M., Oiwane K., Mori T., Yuan D.-Q., and Fujita K. Tetrahedron Lett. 45 (2004) 3383-3386
23. A-sulfonate was estimated from the HPLC peak areas of the two sulfonates.
24. B-allo- or manno-epoxy-CDs. Fujita K., Tahara T., Imoto T., and Koga T. J. Am. Chem. Soc. 108 (1986) 2030-2034
25. Breslow R., and Czarnik A.W. J. Am. Chem. Soc. 105 (1983) 1390-1391
26. Fujita, K. et al., to be published.