Vinyl glycosides in oligosaccharide synthesis (part 5)1: A latent- active glycosylation strategy for the preparation of branched trisaccharide libraries

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9801-9804

  Johnson, Matthew ^a   Arles, Christele ^a   Boons, Geert Jan ^a  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; OLIGOSACCHARIDE; TRISACCHARIDE; UNCLASSIFIED DRUG; VINYLGLYCOSIDE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL STRUCTURE; GLYCOSYLATION; PURIFICATION;

EID: 0032564566     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02177-7     Document Type: Article

References (19)

1. 1. For part 4 see: G.J. Boons, R. Gibson, R. Dickinson, J. Chem. Soc., Perkin Trans. I, 1997, 3357-3360
2. 2. Present address: Complex Carbohydrate Research Center, University of Georgia, Athens, Georgia GA 60602-4712, USA
3. 3. a) M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, E.M. Gordon, J. Med. Chem., 1994, 37, 1233 ;
4. b) M.A. Gallop, R.W. Barrett, W.J. Dower, S.P.A. Fodor, E.M. Gordon, J. Med. Chem., 1994 37, 1385;
5. c) N.K. Terret, M. Gardner, D. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron, 1995, 51, 8135; F. Balkenhohl, C. von dem Bussche-Hünnefeld, Alansky, C. Zechel, Angew. Chem. Int. Ed. Engl., 1996, 35, 2288.
6. c) N.K. Terret, M. Gardner, D. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron, 1995, 51, 8135; F. Balkenhohl, C. von dem Bussche-Hünnefeld, Alansky, C. Zechel, Angew. Chem. Int. Ed. Engl., 1996, 35, 2288.
7. 4. G.J. Boons, B. Heskamp, F. Hout, Angew. Chem. Int. Ed. Engl. 1996, 35, 2845-2847.
8. 5. a) G.J. Boons, S. Isles, Tetrahedron Lett., 3593 (1994);
9. b) G.J. Boons, S. Isles, J. Org. Chem., 1996 61, 4262
10. 6. For other approaches for combinatorial oligosaccharide synthesis see: a) O. Kanie, F. Barresi, Y. Ding, J. Labbe, A. Otter, L.S. Forsberg, B. Ernst, O. Hindsgaul, Angew. Chem., Int. Ed. Engl., 1996, 34, 2;
11. b) J. Gildersleeve, C. Thompson, A. Smith, K. Biswas, W.C. Still, D. Kahne, Science, 1996, 274, 1520,;
12. c) D. Kahne, Current Opinion Chem. Biol, 1997, 1, 130
13. 7. G.J. Boons, S. Isles, A. Burton, Chem Commun., 1996, 141.
14. 8. G.J. Boons, G.H. Castle, J. A. Clase, P. Grice, S.V. Ley and C. Pinel. Synlett, 1993, 913-914.
15. 9. M. Johnson, A. Burton, G.J. Boons, submitted for publication
16. 10. G. Adam, D. Seebach, Synthesis, 1988, 374
17. 11. L. Van, D. Kahne, Synlett, 1995, 523.
18. 12. The trisaccharides were synthesised as individual compounds and it was confirmed that all glycosidic linkages were formed as anomeric mixtures.
19. 13. A portion of the library was treated with aqueous trifluoroacetic acid (2 M solution) at 100°C for 4 hr. Analysis of the resulting mixture on a Dionex HPLC system with a PA1 column and pulsed amperometric detection (PAD) showed the galactose, N-acetyl glycosamine and fucose were present at approximately the required ratio.