Convenient synthesis of an N-glycan octasaccharide of the bisecting type

Journal of Organic Chemistry

Volumn 74, Issue 6, 2009, Pages 2508-2515

  Wang, Guangfa ^a   Zhang, Wei ^a   Lu, Zhichao ^a   Wang, Peng ^a   Zhang, Xiuli ^a   Li, Yingxia ^a  

^a OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2-DEOXY-2; BENZYLIDENE; CHLOROMETHYL; D-GLUCOPYRANOSE; GLUCOPYRANOSIDE; N-GLYCAN; OCTASACCHARIDE;

3,6 DI O BENZYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYLAZIDE DERIVATIVE; BETA DEXTRO MANNOPYRANOSIDE; CARBOHYDRATE DERIVATIVE; ESTER; GLUCOPYRANOSIDE; GLYCAN DERIVATIVE; GLYCOPEPTIDASE; N GLYCAN DERIVATIVE; N GLYCAN OLIGOSACCHARIDE; PYRANOSIDE; UNCLASSIFIED DRUG;

ARTICLE; EPIMERIZATION; GLYCOSYLATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

GLUCOSE; MANNOSE; OLIGOSACCHARIDES; POLYSACCHARIDES;

EID: 64149109669     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900016j     Document Type: Article

References (48)

1. (a) Dwek, R. A. Science 1995, 269, 1234.
2. (b) Dwek, R. A. Chem. Rev. 1996, 96, 683.
3. (c) Van Dijk, W.; Van der Stelt, M. E.; Salera, A.; Dente, L. Eur. J. Cell. Biol. 1991, 55. 143.
4. (d) Shevinskv, L. H.; Knowles, B. B.; Damjanov, I.; Solter, D. Cell 1982, 30, 697.
5. (e) Feizi, T. Nature 1985, 314, 53.
6. (a) Dennis, J. W.; Laferte, S.; Waghorne, C.; Breitman, M. L.; Kerbel, R. S. Science 1987, 236, 582.
7. (b) Zhao, Y.; Nakagawa, T.; Itoh, S.; Inamori, K.; Isaji, T.; Kariya, Y.; Kondo, A.; Mivoshi, E.; Mivazaki, K.; Kawasaki, N.; Taniguchi, N.; Gu, J. J. Biol. Chem. 2006, 281, 32122.
8. (a) Narasimhan, S. J. Biol. Chem. 1982, 257, 10235.
9. (b) Iijima, J.; Zhao, Y.; Isaji, T.; Kameyama, A.; Nakaya, S.; Wang, X. C.; Ihara, H.; Cheng, X.; Nakagawa, T.; Miyoshi, E.; Kondo, A.; Narimatsu, H.; Taniguchi, N.; Gu, J. J. Biol. Chem. 2006, 281, 13038.
10. (c) Zhao, Y.; Sato, Y.; Isaji, T.; Fukuda, T.; Matsumoto, A.; Miyoshi, E.; Gu, J.; Taniguchi, N. FEBS J. 2008, 275, 1939.
11. Yoshimura, M.; Ihara, Y.; Nishiura, T.; Okajima, Y.; Ogawa, M.; Yoshida, H.; Suzuki, M.; Yamamura, K. I.; Kanakura, Y.; Matsuzawa, Y.; Taniguchi, N. Biochem. J. 1998, 331, 733.
12. Ihara, Y.; Sakamoto, Y.; Mihara, M.; Shimizu, K.; Taniguchi, N. J. Biol. Chem. 1997, 272, 9629.
13. (a) Eller, S.; Schuberth, R.; Gundel, G.; Seifert, J.; Unverzagt, C. Angew. Chem., Int. Ed. 2007, 46, 4173.
14. (b) Schuberth, R.; Unverzagt, Chem. Tetrahedron Lett. 2005, 46, 4201.
15. (c) Weiss, H.; Unverzagt, C. Angew. Chem., Int. Ed. 2003, 42, 4261.
16. (d) Unverzagt, C.; Seifert, J. Tetrahedron Lett. 2000, 41, 4549.
17. (a) Barresi, F.; Hindsgaul, O. Can. J. Chem. 1994, 72, 1447.
18. (b) Stork, G.; La Clair, J. L. J. Am. Chem. Soc. 1996, 118, 247.
19. (c) Ito, Y.; Ohnishi, Y.; Ogawa, T.; Nakahara, Y. Synlett 1998, 1102.
20. (a) Dudkin, V. Y.; Crich, D. Tetrahedron Lett. 2003, 44, 1787.
21. (b) Dudkin, V. Y.; Miller, J. S.; Danishefsky, S. J. Tetrahedron Lett. 2003, 44, 1791.
22. (c) Dudkin, V. Y.; Miller, J. S.; Danishefsky, S. J. J. Am. Chem, Soc. 2004, 126, 736.
23. (d) Mandai, H.; Mukaiyama, T. Chem. Lett. 2005, 34, 702.
24. (e) Tanaka, S.; Takashina, M.; Tokimoto, H.; Fujimoto, Y.; Tanaka, K.; Fukase, K. Synlett 2005, 15, 2325.
25. (a) Matsuo, I.; Isomura, M.; Walton, R.; Ajisawa, K. Tetrahedron Lett. 1996, 37, 8795.
26. (b) Li, B.; Zeng, Y.; Hauser, S.; Song, H.; Wang, L. X. J. Am. Chem. Soc. 2005, 127, 9692.
27. (a) Shaban, M. A.; Jeanloz, R. W. Carbohydr. Res. 1976, 52, 115.
28. (b) Warren, C. D.; Auge, C.; Laver, M. L.; Suzuki, S.; Power, D.; Jeanloz, R. W. Carbohydr. Res. 1980, 82, 71.
29. (c) Kerekgvarto, J.; Van der Ven, J. G.; Kamerling, J. P.; Liptak, A.; Vliegenthart. J. F. Carbohydr. Res. 1993, 238, 135.
30. (d) Hiro, S.; Usuki, Y.; Iio, H. Carbohydr. Res. 2006, 341, 1796.
31. (a) Dong, H.; Pei, Z.; Angelin, M.; Bystroem, S.; Ramström, O. J. Org. Chem. 2007, 72, 3694.
32. (b) Dons, H.; Pei, Z.; Ramström, O. J. Org. Chem. 2006, 71, 3306.
33. Varki, A. Glycobiology 1993, 3, 97.
34. (a) Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr Res. 1981, 93, C6.
35. (b) Urban, F. J.; Moore, B. S.; Breitenbach, R. Tetrahedron Lett. 1990, 31, 4421.
36. (c) Wang, W.; Kong, F. J. Org. Chem, 1998, 63, 5744.
37. Yu, H.; Ensley, H. E. Tetrahedron Lett. 2003, 44, 9363.
38. (a) Hou, S. J.; Xu, P.; Zhou, L.; Yu. De Q.; Lei, P. S.; Zou, C. C. Chin. Chem. Lett. 2006, 17, 183.
39. (b) Ennis, S. C.; Gridley, J. J.; Osborn, H. M. I.; Spackman. D. G. Synlett 2000, 11, 1593.
40. (a) Unverzagt, C. Chem, Eur. J. 2003, 9, 1369.
41. (b) Pratt, M. R.; Bertozzi, C. R. J. Am. Chem. Soc. 2003, 125, 6149.
42. Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693.
43. Baeschlin, D. K.; Green, L. G.; Hahn, M. G.; Hinzen, B.; Ince, S. J.; Ley, S. V. Tetrahedron: Asymmetry 2000, 11, 173.
44. (a) Macmillan, D.; Daines, A. M.; Bayrhuber, M.; Flitsch, S. L. Qrg. Lett. 2002, 4, 1467.
45. (b) Grundler, G.; Schmidt, R. R. Carbohydr. Res. 1985, 135, 203.
46. (a) Myszka, H.; Bednarczyk, D.; Najder, M.; Kaca, W. Carbohydr. Res. 2003, 338, 133.
47. (b) Silva, D. J.; Wang, H.; Allanson, N. M.; Jain, R. K.; Sofia, M. J. Org. Chem, 1999, 64, 5926.
48. Seifert, J.; Unverzagt, C. Tetrahedron Lett. 1996, 37, 6527.