Neighboring group participation of 9-anthracenylmethyl group in glycosylation: Preparation of unusual C-glycosides

Journal of Organic Chemistry

Volumn 70, Issue 7, 2005, Pages 2808-2811

  Kulkarni, Suvarn S ^a   Liu, Yi Hung ^b   Hung, Shang Cheng ^b,c  

^a NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^b INSTITUTE OF CHEMISTRY   (Taiwan)

^c NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; CARBON; CHEMICAL ACTIVATION; GLUCOSE; STEREOCHEMISTRY;

9-ANTHRACENYLMETHYL GROUP; GLYCOSYLATION; STEREOSELECTIVITY; THIOGLYCOSIDES;

AROMATIC COMPOUNDS;

ANTHRACENE DERIVATIVE; GLYCOSIDE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; ETHERIFICATION; GLYCOSYLATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

GLYCOSIDES; GLYCOSYLATION;

EID: 17044386574     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo047794a     Document Type: Article

References (39)

1. (a) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503-1531.
2. (b) Davis, B. G. J. Chem. Soc., Perkin Trans. 1 2000, 2137-2160.
3. (c) Carbohydrates in Chemistry and Biology; Ernst, B., Hart, G. W., Sinay, P., Eds.; Wiley-VCH Verlag: Weinheim, 2000; Vol. 1.
4. Veeneman, G. H. In Carbohydrate Chemistry; Boons, G.-J., Ed.; Thomson Science: UK, 1998; Chapter 4.
5. (a) Fraser-Reid, B.; Wu, Z. F.; Udodong, U. E.; Ottoson, H. J. Org. Chem. 1990, 55, 6068-6070.
6. (b) Boons, G.-J. Tetrahedron 1996, 52, 1095-1121.
7. (a) Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019-5087.
8. (b) The Anomeric Effect and Associated Stereoelectronic Effects; Thatcher, G. R. J., Ed.; ACS Syposium Series 539; American Chemical Society: Washington, DC, 1993.
9. Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 37, 1331-1334.
10. Braccini, I.; Derouet, C.; Esnault, J.; Hervé du Penhoat, C.; Mallet, J. M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246, 23-41.
11. For reviews see, (a) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328-334. (b) Ohwada, T. Chem. Rev. 1999, 99, 1337-1375. (c) Jones, G. B. Tetrahedron 2001, 57, 7999-8016.
12. For reviews see, (a) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328-334. (b) Ohwada, T. Chem. Rev. 1999, 99, 1337-1375. (c) Jones, G. B. Tetrahedron 2001, 57, 7999-8016.
13. For reviews see, (a) Gleiter, R.; Paquette, L. A. Acc. Chem. Res. 1983, 16, 328-334. (b) Ohwada, T. Chem. Rev. 1999, 99, 1337-1375. (c) Jones, G. B. Tetrahedron 2001, 57, 7999-8016.
14. Tai, C.-A.; Kulkarni, S. S.; Hung, S.-C. J. Org. Chem. 2003, 68, 8719-8722.
15. Wang, C.-C.; Lee, J.-C.; Luo, S.-Y.; Fan, H.-F.; Pai, C.-L.; Yang, W.-C.; Lu, L.-D.; Hung, S.-C. Angew. Chem., Int. Ed. 2002, 41, 2360-2362.
16. Yang, W.-C.; Lu, X.-A.; Kulkarni, S. S.; Hung, S.-C. Tetrahedron Lett. 2003, 44, 7837-7840.
17. Wang, C.-C.; Luo, S.-Y.; Shie, C.-R.; Hung, S.-C. Org. Lett. 2002, 4, 847-849.
18. Fugedi, P.; Garegg, P. J. Carbohydr. Res. 1986, 149, C9-C12.
19. Tanaka, H.; Sakamoto, H.; Sano, A.; Nakamura, S.; Nakajima, M.; Hashimoto, S. Chem. Commun. 1999, 1259-1260.
20. Selected books and reviews on C-glycosides: (a) Leavy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, 1995. (c) Bertozzi, C. R.; Bednarski, M. D. In Modern Methods in Carbohydrate Synthesis; Harwood Academic Publishers: Reading; 1996; pp 316-351. (d) Du, Y.; Linhardt, R. J.; Vlahow, I. R. Tetrahedron 1998, 54, 9913-9959.
21. Selected books and reviews on C-glycosides: (a) Leavy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, 1995. (c) Bertozzi, C. R.; Bednarski, M. D. In Modern Methods in Carbohydrate Synthesis; Harwood Academic Publishers: Reading; 1996; pp 316-351. (d) Du, Y.; Linhardt, R. J.; Vlahow, I. R. Tetrahedron 1998, 54, 9913-9959.
22. Selected books and reviews on C-glycosides: (a) Leavy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, 1995. (c) Bertozzi, C. R.; Bednarski, M. D. In Modern Methods in Carbohydrate Synthesis; Harwood Academic Publishers: Reading; 1996; pp 316-351. (d) Du, Y.; Linhardt, R. J.; Vlahow, I. R. Tetrahedron 1998, 54, 9913-9959.
23. Selected books and reviews on C-glycosides: (a) Leavy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon: Oxford, 1995. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC: Boca Raton, 1995. (c) Bertozzi, C. R.; Bednarski, M. D. In Modern Methods in Carbohydrate Synthesis; Harwood Academic Publishers: Reading; 1996; pp 316-351. (d) Du, Y.; Linhardt, R. J.; Vlahow, I. R. Tetrahedron 1998, 54, 9913-9959.
24. Ek, M.; Garegg, P. J.; Hultberg, H.; Oscarson, S. J. Carbohydr. Chem. 1983, 2, 305-311.
25. Srivastava, V. K.; Schuerch, C. J. Org. Chem. 1981, 46, 1121-1126.
26. Garegg, P. J.; Iversen, T.; Oscarson, S. Carbohydr. Res. 1976, 50, C12-C-14.
27. Hung, S.-C.; Thopate, S. R.; Chi, F.-C.; Chang, S.-W.; Lee, J.-C.; Wang, C.-C.; Wen, Y.-S. J. Am. Chem. Soc. 2001, 223, 3153-3154.
28. Lee, J.-C.; Lu, X.-A.; Kulkarni, S. S.; Wen, Y.-S.; Hung, S.-C. J. Am. Chem. Soc. 2004, 126, 476-477.
29. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97-101.
30. (a) Martin, O. R. Tetrahedron Lett. 1985, 26, 2055-2058.
31. (b) Martin, O. R. Carbohydr. Res. 1987, 171, 211-222.
32. (c) Martin, O. R.; Mahnken, R. E. J. Chem. Soc., Chem. Commun. 1986, 497-498.
33. (d) Araki, Y.; Mokubo, E.; Kobayashi, N.; Nagasawa. J.; Ishido, Y. Tetrahedron Lett. 1989, 30, 1115-1118.
34. (e) Martin, O. R.; Hendricks, C. A. V.; Deshpande, P. P.; Culter, A. B.; Kane, S. A.; Rao, S. P. Carbohydr. Res. 1990, 196, 41-58.
35. (f) Martin, O. R.; Rao, S. P.; Hendricks, C. A. V.; Mahnken, R. E. Carbohydr. Res. 1990, 202, 49-66.
36. (g) Anastasia, M.; Allevi, P.; Ciuffreda, P.; Fiecchi, A.; Scala, A. Carbohydr. Res. 1990, 208, 264-266.
37. (a) Verlhac, P.; Leteux, C.; Toupet, L.; Veyrières, A. Carbohydr. Res. 1996, 291, 11-20.
38. (b) Rousseau, C.; Martin, O. R. Tetrahedron: Asymmetry 2000, 11, 409-412.
39. (c) Girard, N.; Rousseau, C.; Martin, O. R. Tetrahedron Lett. 2003, 44, 8971-8974.