Challenging deprotection steps during the synthesis of tetra- and pentasaccharide fragments of the LeaLex tumor-associated hexasaccharide antigen

Journal of Organic Chemistry

Volumn 77, Issue 20, 2012, Pages 8864-8878

  Guillemineau, Mickaël ^a   Auzanneau, France Isabelle ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BINDING STUDIES; CARRIER PROTEINS; CHLORINE ATOM; CHLOROACETAMIDES; COMPLEX MIXTURE; CONVERGENT SYNTHESIS; DEPROTECTION; GALACTOSE RESIDUES; GLYCOSYL DONORS; GLYCOSYLATION REACTIONS; HEXASACCHARIDES; METAL DISSOLVING; METHOXIDE IONS; N-DEACYLATION; PENTASACCHARIDES; PROTECTING GROUP; REACTION CONDITIONS; REDUCING ENDS; TETRABUTYLAMMONIUM FLUORIDES; TETRASACCHARIDES; THIOGLYCOSIDES; TRICHLOROACETIMIDATES;

CHLORINE; ESTERIFICATION; GLUCOSE; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

REACTION INTERMEDIATES;

AMMONIUM FLUORIDE; CARBOHYDRATE ANTIGEN; ETHER DERIVATIVE; GALACTOSE; GLYCOSIDE; OLIGOSACCHARIDE; PENTASACCHARIDE; TERT BUTYLDIPHENYLSILYL ETHER; TETRABUTYLAMMONIUM FLUORIDE; TETRASACCHARIDE; THIOGLYCOSIDE; TRICHLOROACETIMIDIC ACID; TUMOR ANTIGEN; TUMOR ASSOCIATED HEXASACCHARIDE ANTIGEN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CONJUGATION; DEACETYLATION; DEPROTECTION REACTION; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

ANTIGENS, TUMOR-ASSOCIATED, CARBOHYDRATE; CARBOHYDRATE SEQUENCE; GLYCOSYLATION; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

EID: 84867696577     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301644w     Document Type: Article

References (35)

1. Buskas, T.; Thompson, P.; Boons, G. J. Chem. Commun. 2009, 5335-5349
2. Astronomo, R. D.; Burton, D. R. Nat. Rev. Drug Discov. 2010, 9, 308-324
3. Morelli, L.; Poletti, L.; Lay, L. Eur. J. Org. Chem. 2011, 5723-5777
4. Hevey, R.; Ling, C. C. Future Med. Chem. 2012, 4, 545-584
5. Liu, C.-C.; Ye, X.-S. Glycoconjugate J. 2012, 29, 259-271
6. Pettijohn, D. E.; Stranahan, P. L.; Due, C.; Roenne, E.; Rahbek, S. H.; Olsson, L. Cancer Res. 1987, 47, 1161-1169
7. Pettijohn, D. E.; Pfenninger, O.; Brown, J.; Duke, R.; Olsson, L. Proc. Natl. Acad. Sci. U.S.A. 1988, 85, 802-806
8. Battifora, H.; Sorensen, H. R.; Mehta, P.; Ahn, C.; Niland, J.; Hage, E.; Pettijohn, D. E.; Olsson, L. Cancer 1992, 70, 1867-1872
9. Stranahan, P. L.; Howard, R. B.; Pfenninger, O.; Cowen, M. E.; Johnston, M. R.; Pettijohn, D. E. Cancer Res. 1992, 52, 2923-2930
10. Stroud, M. R.; Levery, S. B.; Martensson, S.; Salyan, M. E. K.; Clausen, H.; Hakomori, S. Biochemistry 1994, 33, 10672-10680
11. Stranahan, P. L.; Laroe, J.; McCombs, R.; Goldsmith, A.; Rahim, I.; Overland, M.; Pettijohn, D. E. Glycoconjugate J. 1996, 13, 741-747
12. Stranahan, P. L.; Laroe, J.; McCombs, R.; Rahim, I.; Kuhn, C. W.; Pettijohn, D. E. Oncol. Rep. 1998, 5, 235-239
13. Lemieux, R. U.; Baker, D. A.; Weinstein, W. M.; Switzer, C. M. Biochemistry 1981, 20, 199-205
14. Hendel, J. L.; Auzanneau, F.-I. Eur. J. Org. Chem. 2011, 6864-6876
15. Ratner, D. M.; Adams, E. W.; Su, J.; OKeefe, B. R.; Mrksich, M.; Seeberger, P. H. ChemBioChem 2004, 5, 379-382
16. Wang, A.; Auzanneau, F.-I. Carbohydr. Res. 2010, 345, 1216-1221
17. Wang, A.; Hendel, J.; Auzanneau, F.-I. Beilstein J. Org. Chem. 2010, 6 10.3762/bjoc.6.17
18. Lönn, H. Carbohydr. Res. 1985, 139, 105-113
19. Clingman, A. L.; Richtmyer, N. K. J. Org. Chem. 1964, 29, 1782-1787
20. Cao, H.; Huang, S.; Cheng, J.; Li, Y.; Muthana, S.; Son, B.; Chen, X. Carbohydr. Res. 2008, 343, 2863-2869
21. Mong, K. K.; Wong, C. H. Angew. Chem., Int. Ed. 2002, 41, 4087-4090
22. Huang, C. M.; Liu, R. S.; Wu, T. S.; Cheng, W. C. Tetrahedron Lett. 2008, 49, 2895-2898
23. Groneberg, R. D.; Miyazaki, T.; Stylianides, N. A.; Schulze, T. J.; Stahl, W.; Schreiner, E. P.; Suzuki, T.; Iwabuchi, Y.; Smith, A. L.; Nicolaou, K. C. J. Am. Chem. Soc. 1993, 115, 7593-7611
24. Motawi, M. S.; Marcussen, J.; Moller, B. L. J. Carbohydr. Chem. 1995, 14, 1279-1294
25. Yu, H.; Ensley, H. E. Tetrahedron Lett. 2003, 44, 9363-9366
26. Blatter, G.; Jacquinet, J.-C. Carbohydr. Res. 1996, 288, 109-125
27. Hendel, J. L.; Cheng, A.; Auzanneau, F.-I. Carbohydr. Res. 2008, 343, 2914-2923
28. Hendel, J. L.; Wang, J. W.; Jackson, T. A.; Hardmeier, K.; De Los Santos, R.; Auzanneau, F.-I. J. Org. Chem. 2009, 74, 8321-8331
29. Liao, L.; Auzanneau, F.-I. J. Org. Chem. 2005, 70, 6265-6273
30. Cheng, A.; Hendel, J. L.; Colangelo, K.; Bonin, M.; Auzanneau, F.-I. J. Org. Chem. 2008, 73, 7574-7579
31. Bock, K.; Pedersen, C. J. Chem. Soc., Perkin Trans. 2 1974, 293-299
32. Boutet, J.; Guerreiro, C.; Mulard, L. A. J. Org. Chem. 2009, 74, 2651-2670
33. Bartek, J.; Muller, R.; Kosma, P. Carbohydr. Res. 1998, 308, 259-273
34. Kiso, M.; Anderson, L. Carbohydr. Res. 1985, 136, 309-323
35. Deng, S.; Gangadharmath, U.; Chang, C.-W. T. J. Org. Chem. 2006, 71, 5179-5185