Unusual regioselective acylation of the primary hydroxy groups of β-cyclodextrin

Russian Chemical Bulletin

Volumn 52, Issue 1, 2003, Pages 237-246

  Glazyrin, A E ^a   Syrtsev, A N ^a   Kurochkina, G I ^a   Kononov, L O ^b   Grachev, M K ^a   Nifant'ev, E E ^a  

^a MOSCOW STATE PEDAGOGICAL UNIVERSITY   (Russian Federation)

^b N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Acylation; Aliphatic carboxylic acids; Amines; Carboxylic acid chlorides; Cyclodextrins; Inclusion complexes; NMR spectroscopy; Regioselectivity

Indexed keywords

ALIPHATIC COMPOUND; BETA CYCLODEXTRIN; CARBOXYLIC ACID; CHLORIDE; HYDROXYL GROUP; SCAVENGER;

ACETYLATION; ACYLATION; ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PALMITOYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 0037287776     PISSN: 10665285     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1022485407440     Document Type: Article

References (39)

1. J.-M. Lehn, Supramolecular Chemistry. Concepts and Perspectives, VCH Verlagsgesellschaft mbH, Weinheim, 1995; (b) Chem. Rev. (special issue), 1998, 98, No. 5.
2. J.-M. Lehn, Supramolecular Chemistry. Concepts and Perspectives, VCH Verlagsgesellschaft mbH, Weinheim, 1995; (b) Chem. Rev. (special issue), 1998, 98, No. 5.
3. A. R. Khan, P. Forgo, K. J. Stine, and V. T. D'Souza, Chem. Rev., 1998, 98, 1977 (and references cited therein).
4. H. Schlenk, J. L. Gellerman, and D. M. Sand, Anal. Chem., 1962, 84, 1529.
5. P. Zhang, C.-C. Ling, A. W. Coleman, H. Parrot-Lopez, and H. Gallons, Tetrahedron Lett., 1991, 32, 2769.
6. B. Angelova and H.-P. Schmauder, J. Biotechnol., 1999, 67, 13.
7. T. Lacroix, H. Bricout, S. Tilloy, and E. Monflier, Eur. J. Org. Chem., 1999, 3127.
8. R. Widehem, T. Lacroix, H. Bricout, and E. Monflier, Synlett, 2000, 722.
9. H. Bricout, L. Caron, D. Bormann, and E. Monflier, Catal. Today, 2001, 50, 1.
10. K. Uekama, F. Hirayama, and T. Irie, Chem. Rev., 1998, 98, 2045.
11. Y. Kawabata, M. Matsumoto, M. Tanaka, H. Takahashi, Y. Irinatsu, S. Tamura, W. Tagaki, H. Nakahara, and K. Fukuda, Chem. Lett., 1986, 1933.
12. B. J. Ravoo and R. Darcy, Angew. Chem., Int. Ed. Engl., 2000, 39, 4324.
13. A. Janshoff, C. Steinem, A. Michalke, C. Henke, and H. J. Galla, Sens. Actuators, B, 2000, 70, 243.
14. J. Szejtli, Chem. Rev., 1998, 98, 1743.
15. W. Saenger, J. Jacob, K. Gessler, T. Steiner, D. Hoffmann, H. Sanbe, K. Kozumi, S. M. Smith, and T. Tanaka, Chem. Rev., 1998, 98, 1787.
16. G. Wenz, Angew. Chem., Int. Ed. Engl., 1994, 33, 803.
17. A. H. Haines, Adv. Carbohydr. Chem. Biochem., 1976, 33, 11.
18. Y. Tsuda, M. E. Haque, and K. Yoshimoto, Chem. Pharm. Bull., 1983, 31, 1612.
19. M. Therisod and A. M. Klibanov, J. Am. Chem. Soc., 1987, 109, 3977.
20. I. F. Pelyvás, T. K. Lindhorst, H. Streicher, and J. Thiem, Synthesis, 1991, 1015.
21. R. Ishihara, H. Kurihara, and H. Yamamoto, J. Org. Chem., 1993, 58, 3791.
22. T. Ziegler, in Carbohydrate Chemistry, Ed. G.-J. Boons, 1998, Blackie Academic and Professional, London, p. 21.
23. J. Boger, R. J. Corcoran, and J.-M. Lehn, Helv. Chim. Acta, 1978, 61, 2190.
24. A. P. Croft and R. A. Bartsch, Tetrahedron, 1983, 39, 1417 (and references cited therein).
25. N. Sakairi and H. Kuzuhara, Chem. Lett., 1993, 2077.
26. F. Santoyo-Gonzalez, J. Isac-Garcia, A. Vargas-Berenguel, R. Robles-Diaz, and F. G. Calvo-Flores, Carbohydr. Res., 1994, 262, 271.
27. A. Y. Hao, L. H. Tong, F. S. Zhang, and X. M. Gao, Carbohydr. Res., 1995, 277, 333.
28. X. M. Gao, L. H. Tong, Y. Inoue, and A. Tai, Synth. Commun., 1995, 25, 703.
29. S.-H. Chiu and D. C. Myles, J. Org. Chem., 1999, 64, 332.
30. A. A. Sutyagin, A. E. Glazyrin, G. I. Kurochkina, M. K. Grachev, and E. E. Nifant'ev, Zhurn. Obshch. Khim., 2002, 72, 156 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].
31. A. A. Sutyagin, A. E. Glazyrin, G. I. Kurochkina, M. K. Grachev, and E. E. Nifant'ev, Zhurn. Obshch. Khim., 2002, 72, 156 [Russ. J. Gen. Chem., 2002, 72 (Engl. Transl.)].
32. K. Bock and C. Pedersen, Adv. Carbohydr. Chem. Biochem., 1983, 41, 27.
33. A. Ueno and R. Breslow, Tetrahedron Lett., 1982, 23, 3451.
34. K. Fujita, T. Takahara, T. Imoto, and T. Koga, J. Am. Chem. Soc., 1986, 108, 2030.
35. T. Tahara, K. Fujita, and T. Koga, Bull. Chem. Soc. Jpn., 1990, 63, 1409.
36. P. Fügedi, Carbohydr. Res., 1989, 192, 366.
37. S. G. Skoulika, C. A. Georgiou, and M. G. Polissiou, J. Incl. Phenom. Mol. Recognit. Chem., 1999, 34, 85.
38. E. E. Nifant'ev, A. E. Glazyrin, G. I. Kurochkina, and M. K. Grachev, Zhurn. Obshch. Khim., 2000, 70, 1752 [Russ. J. Gen. Chem., 2000, 70 (Engl. Transl.)].
39. E. E. Nifant'ev, A. E. Glazyrin, G. I. Kurochkina, and M. K. Grachev, Zhurn. Obshch. Khim., 2000, 70, 1752 [Russ. J. Gen. Chem., 2000, 70 (Engl. Transl.)].