Facile synthesis of flavonoid 7-O-glycosides

Journal of Organic Chemistry

Volumn 68, Issue 17, 2003, Pages 6842-6845

  Li, Ming ^a   Han, Xiuwen ^a   Yu, Biao ^b  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; REMOVAL; SYNTHESIS (CHEMICAL);

GLYCOSYLATION;

ORGANIC COMPOUNDS;

FLAVONE DERIVATIVE; FLAVONOID; FLAVONOID 7 O GLYCOSIDE DERIVATIVE; FLAVONOID GLYCOSIDE; FLAVONOL DERIVATIVE; IMIDAZOLE; ISOFLAVONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; GLYCOSYLATION; STEREOCHEMISTRY; SYNTHESIS;

CARBOHYDRATE CONFORMATION; FLAVONOIDS; GLYCOSIDE HYDROLASES; IMIDAZOLES; INDICATORS AND REAGENTS;

EID: 0042890563     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034553e     Document Type: Article

References (45)

1. (a) Harborne, J. B. The Flavonoids: Advances in Research since 1986; Chapman and Hall: London, 1994.
2. (b) Harborne, J. B. The Flavonoids: Advances in Research since 1980; Chapman and Hall: London, 1988.
3. (c) Harborne, J. B.; Mabry, T. J. The Flavonoids: Advances in Research; Chapman and Hall: London, 1982.
4. (d) Harborne, J. B.; Mabry, T. J.; Mabry, H. The Flavonoids; Chapman and Hall: London, 1975.
5. Harborne, J. B.; Baxter, H. The Handbook of Natural Flavonoids: John Wiley & Son: Chichester, UK, 1999; Vols. 1 and 2.
6. (a) Shiozaki, M. Tetrahedron: Asymmetry 1999, 10, 1477.
7. (b) Watanabe, Y.; Shiozaki, M.; Kamegai, R. Carbohydr. Res. 2001, 335, 283.
8. Rooke, N.; Li, D.-J.; Li, J.; Keung, W.-M. J. Med. Chem. 2000, 43, 4169.
9. (a) Ichimaru Farukosu, K. K. Japanese Patent 58 225 004/1983; Chem. Abstr. 1984, 100, 126730.
10. (b) Brunke, R. A. GP 443 2947/1996; Chem. Abstr. 1996, 124, 2411803.
11. Park, K. Y.; Lee, S.-H.; Min, B.-K.; Lee, K.-S.; Choi, J.-S.; Chung, S. R.; Min, K. R.; Kim, Y. Planta Med. 1999, 65, 457.
12. Sakamoto, Y.; Ohmoto, T.; Nikaido, T.; Koike, K.; Tomimori, T. Bull. Chem. Soc. Jpn. 1989, 62, 2450.
13. Shimizu, M.; Ito, T.; Terrashima, S.; Hayashi, T.; Arisawa, M.; Morita, N.; Kurokawa, S.; Ito, K.; Hashimoto, Y. Phytochemistry 1984, 23, 1885.
14. (a) Farkas, L.; Mezey-Vándor, G.; Nógrádi, M. Chem. Ber. 1969, 102, 2583.
15. (b) Farkas, L.; Vermes, B.; Nógrádi, M. Chem. Ber. 1972, 105, 3505.
16. (c)Farkas, L.; Mezey-Vándor, G.; Nógrádi, M. Chem. Ber. 1974, 107, 1518.
17. (d) Farkas, L.; Mezey-Vándor, G.; Nógrádi, M. Chem. Ber. 1974, 107, 3878.
18. (e) Mezey-Vándor, G.; Farkas, L.; Nógrádi, M. In Flavonoids and Bioflavonoids Current Research Trends; Farkas, L., Gábor, M., Kállay, F., Eds.: Elsevier: Amsterdam, 1977; pp 187-192.
19. (f) Mezey-Vándor, G.; Farkas, L.; Kanzel, I.; Nógrádi, M. Chem Ber. 1980, 113, 1945.
20. (g) Demetzos, C.; Skaltsounis, A. L.; Tillequin, F.; Koch, M. Carbohydr. Res. 1990, 207, 131.
21. (h) Alluis, B.; Dangles, O. Helv. Chim. Acta 1999, 82, 2201.
22. (i) Alluis, B.; Dangles, O. Helv. Chim. Acta 2001, 84, 1133.
23. (j) Kondo, T.; Oyama, K.-I.; Yoshida, K. Angew. Chem., Int. Ed. 2001, 40, 894.
24. Needs, P. W.; Williamson, G. Carbohydr. Res. 2001, 330, 511.
25. Shin, J.-S.; Kim, K.-S.; Kim, M.-B.; Jeong, J.-H.; Kim, B.-K. Bioorg. Med. Chem. Lett. 1999, 9, 869.
26. (a) Chakraborti, A. K.; Nayak, M. K.; Sharma, L. ¿ J. Org. Chem. 1999, 64, 8027.
27. (b) Chakraborti, A. K.; Sharma, L.; Nayak, M. K. ¿ J. Org. Chem. 2002, 67, 2541.
28. Li, M.; Han, X.-W.; Yu, B. Tetrahedron Lett. 2002, 43, 9467.
29. Reich, H. J.; Rigby, J. H. Handbook of Reagents for Organic Synthesis: Acidic and Basic Reagents; John Wiley & Son: Chichester, UK, 1999.
30. Kaljurand, I.; Rodima, T.; Leito, I.; Koppel, I. A.; Schwesinger, R. J. Org. Chem. 2000, 66, 6202.
31. Leffek, K.; Przuszynski, P.; Thanapaalasingham, K. Can. J. Chem. 1989, 67, 590.
32. (a) Yamaguchi, M.; Horiguchi, A.; Fukuda, A.; Minami, T. J. Chem. Soc., Perkin Trans. 1 1990, 1079.
33. (b) Oyama, K.-I.; Kondo, T. Synlett 1999, 1627.
34. (c) Lee, Y. S.; Rho, E. S.; Min, Y. K.; Kim, B. T.; Kim, K. H. J. Carbohydr. Chem. 2001, 20, 503.
35. Clerici, F.; Gelmi, M. L.; Mottadelli, S. J. Chem. Soc., Perkin Trans. 1 1994, 985.
36. (a) Jensen, K. J.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1993, 2119.
37. (b) Vargas-Berenguel, A.; Meldal, M.; Paulsen, H.; Jensen, K. J.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1994, 3287.
38. (a) Yu, B.; Tao, H. Tetrahedron Lett. 2001, 42, 2405.
39. (c) Yu, B.; Tao, H. J. Org. Chem. 2002, 67, 9099.
40. (a) Jurd, L.; Rolle, L. A. J. Am. Chem. Soc. 1958, 80, 5527.
41. (b) Simpson, T. H.; Wright, R. S. J. Org. Chem. 1961, 26, 4686.
42. (c) Vermes, B.; Farkas, L.; Nógrádi, M. In Topics in Flavonoid Chemistry and Biochemistry; Farkas, L., Gábor, M., Kállay, F., Eds.: Akademiai: Budapest; Elsevier: Amsterdam, 1975; pp 162-170.
43. (d) Kurosawa, K. Bull. Chem. Soc. Jpn. 1970, 43, 2176.
44. (a) Rajananda, V.; Brown, S. B. Tetrahedron Lett. 1981, 22, 4331.
45. (b) Balogh-Hergovich, P.; Speier, G. J. Org. Chem. 2001, 66, 7974.