Efficient methods for glycosidations with glycals - A key intermediate for the synthesis of mucin core 1-type O-glycan

Synlett

Volumn , Issue 5, 2004, Pages 836-840

  Geiger, Jürgen ^a   Barroca, Nadine ^a   Schmidt, R R ^a  

^a UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Carbohydrates; Glycols; Glycopeptides; Glycosylation; Michael additions; Nitro reduction

Indexed keywords

GLYCAN DERIVATIVE; LEWIS ACID; MUCIN; THREONINE; TRICHLOROACETIMIDIC ACID;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; GLYCOSIDATION; NITRATION; REDUCTION; STEREOCHEMISTRY;

EID: 1942425168     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817790     Document Type: Article

References (34)

1. Collins, P. M.; Ferrier, R. J. Monosaccharides, their Chemistry and their Roles in Natural Products; John Wiley and Sons: Chichester UK, 1995, 317-326.
2. (2) Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380; Angew. Chem. 1996, 108, 1482.
3. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380; Angew. Chem. 1996, 108, 1482.
4. Izumi, M.; Ichikawa, Y. Tetrahedron Lett. 1998, 39, 2079.
5. (a) Lichtenthaler, F. W. In Modern Synthetic Methods; Scheffold, R., Ed.; VCH: Weinheim, 1992, 273-376. (b) Bols, M. Carbohydrate Building Blocks; Wiley: New York, 1996, 49-53.
6. (a) Lichtenthaler, F. W. In Modern Synthetic Methods; Scheffold, R., Ed.; VCH: Weinheim, 1992, 273-376. (b) Bols, M. Carbohydrate Building Blocks; Wiley: New York, 1996, 49-53.
7. Varki, A. Glycobiology 1993, 3, 97.
8. Brockhausen, I. Biochem. Biophys. Acta 1999, 1473, 67.
9. Brocke, C.; Kunz, H. Bioorg. Med. Chem. 2002, 10, 3085.
10. (a) Das, J.; Schmidt, R. R. Eur. J. Org. Chem. 1998, 1609.
11. (b) Winterfeld, G. A.; Ito, Y.; Ogawa, T.; Schmidt, R. R. Eur. J. Org. Chem. 1999, 1167.
12. (c) Winterfeld, G. A.; Khodair, A. I.; Schmidt, R. R. Eur. J. Org. Chem. 2003, 1009.
13. (d) Khodair, A. I.; Schmidt, R. R. Eur. J. Org. Chem. in press.
14. (e) Pachamuthu, K.; Gupta, A.; Das, J.; Schmidt, R. R. Eur. J. Org. Chem. 2002, 1479.
15. (f) Pachamuthu, K.; Schmidt, R. R. Synlett 2003, 1355.
16. (g) Winterfeld, G. A.; Das, J.; Schmidt, R. R. Eur. J. Org. Chem. 2000, 3047.
17. See for example: (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661. (b) Liu, K. K.-C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (c) Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126.
18. See for example: (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661. (b) Liu, K. K.-C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (c) Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126.
19. See for example: (a) Halcomb, R. L.; Danishefsky, S. J. J. Am. Chem. Soc. 1989, 111, 6661. (b) Liu, K. K.-C.; Danishefsky, S. J. J. Org. Chem. 1994, 59, 1892. (c) Zheng, C.; Seeberger, P. H.; Danishefsky, S. J. J. Org. Chem. 1998, 63, 1126.
20. Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840.
21. (11) Winterfeld, G. A.; Schmidt, R. R. Angew. Chem. Int. Ed. 2001, 40, 2654; Angew. Chem. 2001, 113, 2718.
22. Winterfeld, G. A.; Schmidt, R. R. Angew. Chem. Int. Ed. 2001, 40, 2654; Angew. Chem. 2001, 113, 2718.
23. Danishefsky, S. J.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Koseki, K.; Griffith, D. A.; Oriyama, T.; Marsden, S. P. J. Am. Chem. Soc. 1995, 117, 1940.
24. Danishefsky, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O. J. Am. Chem. Soc. 1995, 117, 5701.
25. Randolph, J. T.; McClure, K. F.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 5712.
26. 3N was added. Evaporation of the solvent and purification by chromatography on silica gel yielded the target disaccharide.
27. 1,2 = 3.6 Hz].
28. Belot, F.; Rabuka, D.; Fukuda, M.; Hindsgaul, O. Tetrahedron Lett. 2002, 43, 7743.
29. Following one referee, this result may be due to nitration of Fmoc.
30. Oppolzer, W.; Tamura, O. Tetrahedron Lett. 1990, 31, 991.
31. 2O in pyridine) of the residue followed by concentration of the mixture and purification by chromatography on silica gel afforded the corresponding N-acetamido glycoside.
32. (a) Lüning, B.; Norberg, T.; Tejbrant, I. Glycoconjugate J. 1989, 6, 5.
33. (b) Leuck, M.; Kunz, H. J. Prakt. Chem. 1997, 322.
34. (c) Matthieux, N.; Paulsen, H.; Meldal, M.; Bock, K. J. Chem. Soc., Perkin Trans. 1 1997, 2359.