New large-scale preparations of versatile 6-O-monotosyl and 6-monohydroxy permethylated α-, β-, and γ-cyclodextrins

Chemistry Letters

Volumn , Issue 5, 2002, Pages 514-515

  Kaneda, Takahiro ^a   Fujimoto, Tatsuhiko ^a   Goto, Jun'ichiro ^a   Asano, Kaori ^a   Yasufuku, Yoshitaka ^a   Jung, Jone Hwa ^a   Hosono, Chiaki ^a   Sakata, Yoshiteru ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; GAMMA CYCLODEXTRIN;

ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; METHYLATION; SYNTHESIS; TEMPERATURE;

EID: 0036306203     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.514     Document Type: Article

References (30)

1. For a review: R. Breslow and S. D. Dong, Chem. Rev., 98, 1997 (1998).
2. For a review: A. Harada, Acc. Chem. Res., 34, 456 (2001).
3. For reviews, see: a) A. P. Croft and R. A. Bartsch, Tetrahedron, 39, 1417 (1983). b) L. Jicsinszky, E. Fenyvesi, H. Hashimoto, and A. Ueno, "Cyclodextrin Derivatives," in "Comprehensive Supramolecular Chemistry," ed. by J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Pergamon, Oxford (1996), Vol. 3, p 57. c) A. R. Khan, P. Forgo, K. J. Stine, and V. T. D'Souza, Chem. Rev., 98, 1977 (1998). d) C. J. Easton and S. F. Lincoln, "Modified Cyclodextrins," Imperial College Press, London (1999). J. Szejtli, A. Liptak, I. Jodal, P. Fugedi, P. Nanasi, and A. Neszmelyi, Starch, 32, S 165 (1980).
4. For reviews, see: a) A. P. Croft and R. A. Bartsch, Tetrahedron, 39, 1417 (1983). b) L. Jicsinszky, E. Fenyvesi, H. Hashimoto, and A. Ueno, "Cyclodextrin Derivatives," in "Comprehensive Supramolecular Chemistry," ed. by J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Pergamon, Oxford (1996), Vol. 3, p 57. c) A. R. Khan, P. Forgo, K. J. Stine, and V. T. D'Souza, Chem. Rev., 98, 1977 (1998). d) C. J. Easton and S. F. Lincoln, "Modified Cyclodextrins," Imperial College Press, London (1999). J. Szejtli, A. Liptak, I. Jodal, P. Fugedi, P. Nanasi, and A. Neszmelyi, Starch, 32, S 165 (1980).
5. For reviews, see: a) A. P. Croft and R. A. Bartsch, Tetrahedron, 39, 1417 (1983). b) L. Jicsinszky, E. Fenyvesi, H. Hashimoto, and A. Ueno, "Cyclodextrin Derivatives," in "Comprehensive Supramolecular Chemistry," ed. by J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Pergamon, Oxford (1996), Vol. 3, p 57. c) A. R. Khan, P. Forgo, K. J. Stine, and V. T. D'Souza, Chem. Rev., 98, 1977 (1998). d) C. J. Easton and S. F. Lincoln, "Modified Cyclodextrins," Imperial College Press, London (1999). J. Szejtli, A. Liptak, I. Jodal, P. Fugedi, P. Nanasi, and A. Neszmelyi, Starch, 32, S 165 (1980).
6. For reviews, see: a) A. P. Croft and R. A. Bartsch, Tetrahedron, 39, 1417 (1983). b) L. Jicsinszky, E. Fenyvesi, H. Hashimoto, and A. Ueno, "Cyclodextrin Derivatives," in "Comprehensive Supramolecular Chemistry," ed. by J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Pergamon, Oxford (1996), Vol. 3, p 57. c) A. R. Khan, P. Forgo, K. J. Stine, and V. T. D'Souza, Chem. Rev., 98, 1977 (1998). d) C. J. Easton and S. F. Lincoln, "Modified Cyclodextrins," Imperial College Press, London (1999). J. Szejtli, A. Liptak, I. Jodal, P. Fugedi, P. Nanasi, and A. Neszmelyi, Starch, 32, S 165 (1980).
7. For reviews, see: a) A. P. Croft and R. A. Bartsch, Tetrahedron, 39, 1417 (1983). b) L. Jicsinszky, E. Fenyvesi, H. Hashimoto, and A. Ueno, "Cyclodextrin Derivatives," in "Comprehensive Supramolecular Chemistry," ed. by J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, and J.-M. Lehn, Pergamon, Oxford (1996), Vol. 3, p 57. c) A. R. Khan, P. Forgo, K. J. Stine, and V. T. D'Souza, Chem. Rev., 98, 1977 (1998). d) C. J. Easton and S. F. Lincoln, "Modified Cyclodextrins," Imperial College Press, London (1999). J. Szejtli, A. Liptak, I. Jodal, P. Fugedi, P. Nanasi, and A. Neszmelyi, Starch, 32, S 165 (1980).
8. a) J. H. Jung, C. Takehisa, Y. Sakata, and T. Kaneda, Chem. Lett., 1996, 147.
9. b) T. Fujimoto, Y. Uejima, H. Imaki, J. H. Jung, Y. Sakata, and T. Kaneda, Chem. Lett., 2000, 564.
10. c) T. Fujimoto, Y. Sakata, and T. Kaneda, Chem. Lett., 2000, 764.
11. d) T. Fujimoto, Y. Sakata, and T. Kaneda, Chem. Commun., 2000, 2143.
12. e) T. Fujimoto, A. Nakamura, Y. Inoue, Y. Sakata, and T. Kaneda, Tetrahedron Lett., 42, 7987 (2001).
13. f) T. Kaneda, T. Yamada, T. Fujimoto, and Y. Sakata, Chem. Lett., 2001, 1264.
14. M. Tanaka, Y. Kawaguchi, T. Niinae, and T. Shono, J. Chromatogr., 314, 193 (1984). The overall yields, the scale of the experiments, and the characterizations were not provided.
15. G. Yi, J. S. Bradshaw, B. E. Rossiter, and A. Malik, J. Org. Chem., 58, 4844 (1993).
16. Z. Chem, J. S. Bradshaw, and M. L. Lee, Tetrahedron Lett., 37, 6831 (1996).
17. N. Lupescu, C. K. Y. Ho, G. Jia, and J. J. Krepinsky, J. Carbohyd. Chem., 18, 99 (1999).
18. J. H. Jung, K. Asano, T. Sugimoto, C. Hosono, Y. Sakata, and T. Kaneda, unpublished work.
19. N. Kornblum, W. J. Jones, and G. J. Anderson, J. Am. Chem. Soc., 81, 4113 (1959).
20. D. Melton and K. N. Slessor, Carbohydr. Res., 18, 29 (1971).
21. H. C. Jarrell, R. G. S. Ritchie, W. A. Szarek, and J. K. N. Jones, Can. J. Chem., 51, 1767 (1973).
22. 2OTs), 3.9-3.1 (m, 114H), 3.04 (dd, J = 9.6, 3.1 Hz, 1H), 2.45 (s, 3H, OTs).
23. a) Y. Matsui and A. Okimoto, Bull. Chem. Soc. Jpn., 51, 3030 (1971).
24. b) Onozuka, M. Kojima, K. Hattori, and F. Toda, Bull. Chem. Soc. Jpn., 53, 3221 (1980).
25. c) S. Onozuka, M. Kojima, K. Hattori, and F. Toda, Tetrahedron Lett., 23, 3451 (1982).
26. d) N. Zhong, H.-S. Byun, and R. Bittman, Tetrahedron Lett., 39, 2919 (1998).
27. e) B. Brady, N. Lynam, T. O'Sullivan, C. Ahern, and R. Darcy, Org. Synth., 77, 220 (2000).
28. f) H.-S. Byun, N. Zhong, and R. Bittman, Org. Synth., 77, 225 (2000).
29. a) K. Takahashi and K. Hattori, J. Incl. Phenom., 2, 661 (1984).
30. K. Fujita, T. Tahara, T. Imoto, and T. Koga, Chem. Lett., 1988, 1329.