Stereoselective glycosylation and oligosaccharide synthesis on solid support using a 4-azido-3-chlorobenzyl group for temporary protection

Synlett

Volumn , Issue 1, 2000, Pages 27-32

  Egusa, Kenji ^a   Fukase, Koichi ^a   Nakai, Yoshihiko ^a   Kusumoto, Shoichi ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Macroporous polystyrene; Oxidative deprotection; Solid phase synthesis; Thioglycosides

Indexed keywords

BENZOQUINONE DERIVATIVE; CHLOROBENZOIC ACID DERIVATIVE; GLUCOSE DERIVATIVE; OLIGOSACCHARIDE; POLYSTYRENE; THIOGLYCOSIDE; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; GLYCOSYLATION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033978056     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. For recent advances in solid phase chemical synthesis of oligosaccharide: (a) Verduyn, R.; van der Klein, P. A. M.; Douwes, M.; van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1993, 112, 464.
2. (b) Danishefsky, S. J.; McClure, K. F.; Randolph, J. T.; Ruggeri, R. B. Science 1993, 260, 1307.
3. (c) Yan, L.; Taylor, C. M.; Goodnow, R.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 6953.
4. (d) Douglas, S. P.; Whitfield, D. M.; Krepinsky, J. J. J. Am. Chem. Soc. 1995, 117, 2116.
5. (e) Randolph, J. T.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5712.
6. (f) Ito, Y.; Kanie, O.; Ogawa, T. Angew. Chem. Int. Ed. Engl. 1996, 35, 2510.
7. (g) Rademann, J.; Schmidt, R. R. Tetrahedron Lett. 1996, 37, 3989.
8. (h) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; DeRoose, F. J. Am. Chem. Soc. 1997, 119, 449.
9. (i) Rademann, J.; Schmidt, R. R. J. Org. Chem. 1997, 62, 3650.
10. (j) Rodebaugh, R.; Joshi, S.; Fraser-Reid, B.; Geysen, H. M. J. Org. Chem. 1997, 62, 5660.
11. (k) Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126.
12. (l) Heckel, A.; Mross, E.; Jung, K. -H.; Rademann, J.; Schmit, R.R. Synlett 1998, 171.
13. Fukase, K.; Egusa, K.; Nakai, Y.; Kusumoto, S. Molecular Diversity 1996, 2, 182.; Egusa, K.; Fukase, K.; Kusumoto, S. Synlett 1997, 675.
14. Fukase, K.; Egusa, K.; Nakai, Y.; Kusumoto, S. Molecular Diversity 1996, 2, 182.; Egusa, K.; Fukase, K.; Kusumoto, S. Synlett 1997, 675.
15. Oikawa, Y.; Yoshioka, T.; Yonemitsu, O. Tetrahedron Lett. 1982, 23, 885.
16. Commercially available from Argonaut Technologies, San Carlos, California: http://www.argotech.com. For investigations of other highly crosslinked macroporous resins, see: Hori, M.; Gravert, D. J.; Wentworth, P., Jr.; Janda, K. D. Bioorg. Med. Chem. Lett. 1998, 8, 2363.
17. Fukase, K.; Nakai, Y.; Egusa, K.; Porco, J. A.; Kusumoto, S. Synlett 1999, 1074.
18. Fukase, K.; Nakai, Y.; Kanoh, T.; Kusumoto, S. Synlett 1998, 85.
19. Glycosylation using thioglycosides and NBS: Fukase, K.; Hasuoka, A.; Kinoshita, I.; Aoki, Y.; Kusumoto, S. Tetrahedron. 1995, 51, 4923.
20. Glycosylation using thioglycosides and PhIO: Fukase, K.; Kinoshita, I.; Kanoh, T.; Nakai, Y.; Hasuoka, A.; Kusumoto, S. Tetrahedron. 1996, 52, 3897.
21. The yield was based on the weight gain.
22. + form), then concentrated in vacuo. The residue was purified by preparative thin layer chromatography (hexane-ethyl acetate 1:1) to afford saccharide 9 (32 mg, 52μmol) as white crystals.
23. Wang, L.-X.; Sakairi, N.; Kuzuhara, H. J. Chem. Soc., Perkin Trans' 1990, 1677.
24. 2 twice, then dried in vacuo. This procedure was repeated once more to complete the reaction, and the solid-supported disaccharide 16-ArgoPore™ (80 mg) was obtained as a slightly brown powder. The disaccharide 18 was cleaved from the solid support by the procedure described in Note (10).
25. ArgoPore™ low load (0.28 mmol/g) was used for the tetrasaccharide synthesis. On the conventional ArgoPore™ (0.70 mmol/g), the yields of the second step glycosylation to form the trisaccharide were much lower than those of the first step glycosylation to form the disaccharide. In the case of the ArgoPore™ low load, by contrast, such difference in reactivity on each glycosylation step was much less significant, though some of the glycosyl acceptors remained unchanged in each step.
26. 2, then dried in vacuo to give solid-supported disaccharide 20 (243 mg) as a slightly brown powder.
27. 4.
28. 4), 2.09 (3H, s, Ac), 2.05 (3H, s, Ac), 2.03 (3H, s, Ac), 2.01 (3H, s, Ac), 1.99 (3H, s, Ac), 1.98 (3H, s, Ac), 1.98 (3H, s, Ac), 1.97 (3H, s, Ac), 1.97 (3H, s, Ac), 1.91 (3H, s,
29. 4.
30. A drawback of the macroporous resin, ArgoPore™, was the presence of non-reactive glycosyl acceptors on it owing to the heterogeneity in the pore size. When dry, ArgoPore™ has an average pore size of approximately 90 Å, which is large enough for oligosaccharide synthesis, but the presence of an unnegligible portion of smaller pores of the resin may cause the difference in reactivity of glycosyl acceptors. Steric hindrance of the resin itself in smaller pores may hinder glycosylation. Recently, we succeeded in the selective loading of a glycosyl acceptor to reactive sites, i.e., the surface of large pores by decreasing the loading levels. This may lead to higher total yields of synthesis by introducing the first monosaccharide unit 8 only to reactive site on the macroporous resin.