Synthesis of a new type of D-mannosamine glycosyl donor and acceptor and their use for the preparation of oligosaccharides consisting of D-mannosamine units linked by α(1→4)-glycosidic bonds

Synthesis

Volumn , Issue 16, 2008, Pages 2610-2616

  Turský, Matyáš ^a,b,c   Veselý, Jan ^a   Tišlerová, Iva ^a   Trnka, Tomáš ^a   Ledvina, Miroslav ^b  

^a CHARLES UNIVERSITY   (Czech Republic)

^b INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^c TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

Carbohydrates; D mannosamine; Glycosylation; Oligosaccharides

Indexed keywords

CARBOHYDRATES; D-MANNOSAMINE; GLYCOSYLATION; MANNOSAMINE; SYNTHESIS OF;

OLIGOSACCHARIDES;

4 O ACETYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA,BETA DEXTRO MANNOPYRANOSE; ALLYL 2 AZIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSYL (1-4) 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 3 O BENZYL 4,6 O BENZYLIDENE 2 (NONAFLUOROBUTANESULFONYL) ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 3 O BENZYL 4,6 O BENZYLIDENE 2 O METHANESULFONYL ALPHA DEXTRO GLUCOPYRANOSIDE; ALLYL 3 O BENZYL 4,6 O BENZYLIDENE 2 O TRIFLUOROMETHANESULFONYL ALPHA DEXTRO GLUCOPYRANOSIDE; ALLYL 3 O BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; ALLYL 4 O ACETYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 4 O ACETYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSYL (1-4) 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 4 O ACETYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSYL (1-4) 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSYL (1-4) 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSIDE; ALLYL 4,6 O BENZYLIDENE ALPHA DEXTRO GLUCOPYRANOSIDE; ALLYL ALPHA DEXTRO GLUCOPYRANOSIDE; GLYCOSIDE; MANNOSAMINE; O (4 O ACETYL 2 AZIDO 3,6 DI O BENZYL 2 DEOXY ALPHA DEXTRO MANNOPYRANOSYL)TRICHLOROACETIMIDATE; OLIGOSACCHARIDE; PYRANOSIDE; TRISACCHARIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 50849115492     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067197     Document Type: Article

References (25)

1. Dwek, R. A. Chem. Rev. 1996, 96, 683.
2. Varki, A. Glycobiology 1993, 3, 97.
3. Bongat, A. F. G.; Demchenko, A. V. Carbohydr. Res. 2007, 342, 374.
4. Banoub, J.; Boullanger, P.; Lafont, D. Chem. Rev. 1992, 92, 1167.
5. Gridley, J. J.; Osborn, H. M. I. J. Chem. Soc., Perkin Trans. 1 2000, 10, 1471.
6. Veselý, J.; Ledvina, M.; Jindřich, J.; Trnka, T.; Šaman, D. Collect. Czech. Chem. Commun. 2004, 69, 1914.
7. Beynon, L. M.; Richards, J. C.; Perry, M. B.; Kniskern, P. J. Can. J. Chem. 1992, 70, 218.
8. Osa, Y.; Kaji, E.; Takahashi, K.; Hirooka, M.; Zen, S.; Lichtenthaler, F. W. Chem. Lett. 1993, 1567.
9. Silipo, A.; Molinaro, A.; Lanzetta, R.; Parrilli, M.; Lindner, B.; Holst, O. Eur. J. Org. Chem. 2004, 1336.
10. Litjens, R. E. J. N.; Leeuwenburgh, M. A.; van der Marel, G. A.; van Boom, J. H. Tetrahedron Lett. 2001, 42, 8693.
11. Litjens, R. E. J. N.; van den Bos, L. J.; Codée, J. D. C.; van den Berg, R. J. B. H. N.; Overkleeft, H. S.; van der Marel, G. A. Eur. J. Org. Chem. 2005, 918.
12. van den Bos, L. J.; Duivenvoorden, B. A.; de Koning, M. C.; Filippov, D. V.; Overkleeft, H. S.; van der Marel, G. A. Eur. J. Org. Chem. 2007, 116.
13. Crich, D.; Chandrasekera, N. S. Angew. Chem. Int. Ed. 2004, 43, 5386.
14. Veselý, J.; Rohlenová, A.; Dýžoganová, M.; Trnka, T.; Tišlerová, I.; Šaman, D.; Ledvina, M. Synthesis 2006, 699.
15. Schmidt, R. R.; Kinzy, W. Adv. Carbohydr. Chem. Biochem. 1994, 50, 21.
16. Gin, D. J. Carbohydr. Chem. 2002, 21, 645.
17. Tanaka, H.; Kawai, K.; Fujiwara, K.; Murai, A. Tetrahedron 2002, 58, 10017.
18. Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145.
19. Codée, J. D. C.; van den Bos, L. J.; Litjens, R. E. J. N.; Overkleeft, H. S.; van Boeckel, C. A. A.; van Boom, J. H.; van der Marel, G. A. Tetrahedron 2004, 60, 1057.
20. Gattuso, G.; Nepogodiev, S. A.; Stoddart, J. F. Chem. Rev. 1998, 98, 1919.
21. Hofman-Bang, N. Acta Chem. Scand. 1957, 11, 581.
22. Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1996, 287, 169.
23. Holme, K. R.; Hall, L. D. Carbohydr. Res. 1992, 225, 291.
24. Fukase, K.; Matsumoto, T.; Ito, N.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull. Chem. Soc. Jpn. 1992, 65, 2643.
25. Peer, A.; Vasella, A. Helv. Chim. Acta 1999, 82, 1044.