Efficient polymer-assisted strategy for the deprotection of protected oligosaccharides

Angewandte Chemie - International Edition

Volumn 45, Issue 38, 2006, Pages 6349-6352

  Tanaka, Hiroshi ^a   Ishida, Tadasuke ^a   Matoba, Nobuatsu ^a   Tsukamoto, Hirokazu ^a,b   Yamada, Haruo ^a,c   Takahashi, Takashi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

^c OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Birch reduction; Glycoconjugates; Glycosylation; Oligosaccharides; Solid phase synthesis

Indexed keywords

BIRCH REDUCTION; GLYCOCONJUGATES; GLYCOSYLATION; OLIGOSACCHARIDES; SOLID-PHASE SYNTHESIS;

ACETIC ACID; CHEMICAL MODIFICATION; SUGARS; SYNTHESIS (CHEMICAL);

OLIGOMERS;

OLIGOSACCHARIDE; POLYMER;

ARTICLE; CARBOHYDRATE ANALYSIS; CHEMISTRY; CONFORMATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MOLECULAR GENETICS;

CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES; POLYMERS;

EID: 33749247250     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200601128     Document Type: Article

References (28)

1. a) A. Varki, Glycobiology 1993, 3, 97-130;
2. b) R. A. Dwek, Chem. Rev. 1996, 96, 683-720;
3. c) S. Hakomori, Arch. Biochem. Biophys. 2004, 426, 173-181;
4. d) I. Bucior, M. M. Burger, Curr. Opin. Struct. Biol. 2004, 14, 631-637.
5. P. H. Seeberger, W.-C. Haase, Chem. Rev. 2000, 100, 4349-4393.
6. The solid-supported benzyl ethers are known to be difficult to cleave, a) O. Kanie, G. Grotenbreg, C.-H. Wong, Angew. Chem. 2000, 112, 4719-4721;
7. Angew. Chem. Int. Ed. 2000, 39, 4545-4547;
8. b) M. Adinolfi, G. Barone, A. Iadonisi, M. Schiattarella, Tetrahedron Lett. 2001, 42, 5971-5972.
9. L. A. Thompson, J. A. Ellman, Tetrahedron Lett. 1994, 35, 9333-9336.
10. The THP linker is not amenable to the solid-phase synthesis of oligosaccharides because it is not stable under acidic glycosidation conditions.
11. a) A. Matsuda, T. Doi, H. Tanaka, T. Takahashi, Synlett 2001, 1101-1104;
12. b) H. Tanaka, T. Zenkoh, H. Setoi, T. Takahashi, Synlett 2002, 1427-1430.
13. B. Meseguer, D. Alonso-Díaz, N. Griebenow, T. Herget, H. Waldmann, Angew. Chem. 1999, 111, 3083-3087;
14. Angew. Chem. Int. Ed. 1999, 38, 2902-2906.
15. S. Hakomori, Y. Zhang, Chem. Biol. 1997, 4, 97.
16. For reports of the chemical synthesis of dimeric Lewis X, see a) S. Sato, Y. Ito, T. Ogawa, Tetrahedron Lett. 1988, 29, 5267-5270;
17. b) A. Kameyama, T. Ehara, Y. Yamada, H. Ishida, M. Kiso, A. Hasegawa, J. Carbohydr. Chem. 1995, 14, 507.
18. For reports of the chemical synthesis of trimeric Lewis X, see a) K. C. Nicolaou, T. J. Caulfield, H. Kataoka, N. A. Stylianides, J. Am. Chem. Soc. 1990, 112, 3693-3695;
19. b) A. Toepfer, W. Kinzy, R. R. Schmidt, Liebigs Ann. Chem. 1994, 449-464;
20. c) W. Broder, H. Kunz, Bioorg. Med. Chem. 1997, 5, 1-19;
21. d) K. M. Köeller, C.-H. Wong, Chem. Eur. J. 2000, 6, 1243-1251.
22. a) T. Kanemitsu, O. Kanie, C.-H. Wong, Angew. Chem. 1998, 110, 3574-3577;
23. Angew. Chem. Int. Ed. 1998, 37, 3415-3418;
24. b) T. Zhu, G.-J. Boons, J. Am. Chem. Soc. 2000, 122, 10 222-10 223;
25. c) K. R. Love, P. H. Seeberger, Angew. Chem. 2004, 116, 612-615;
26. Angew. Chem. Int. Ed. 2004, 43, 602-605.
27. H. Tanaka, N. Matoba, H. Tsukamoto, H. Takimoto, H. Yamada, T. Takahashi, Synlett 2005, 824-828.
28. 2O/EtOH (1:5) at reflux for 12 h did not reduce the loading amount of the solid-supported 10 a. These results indicated that the THP linker could be stable during cleavage of the phthalyl groups.