Scope and limitations of imidazolium-based ionic liquids as room temperature glycosylation promoters

Carbohydrate Research

Volumn 345, Issue 1, 2010, Pages 45-49

  Galan, M Carmen ^a   Jouvin, Kevin ^a   Alvarez Dorta, Dimitri ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

Glycosylation at room temperature; Ionic liquids; Oligosaccharide synthesis

Indexed keywords

COUNTERIONS; GLYCOSYLATION REACTIONS; IMIDAZOLIUM CATION; IMIDAZOLIUM-BASED IONIC LIQUID; N-IODOSUCCINIMIDE; OLIGOSACCHARIDE SYNTHESIS; ROOM TEMPERATURE; ROOM TEMPERATURE IONIC LIQUIDS; THIOGLYCOSIDES;

ESTERIFICATION; GLYCOSYLATION; IONIZATION OF LIQUIDS; IONS; OLIGOSACCHARIDES;

IONIC LIQUIDS;

IMIDAZOLE DERIVATIVE; IONIC LIQUID; THIOGLYCOSIDE;

ARTICLE; CHEMICAL STRUCTURE; GLYCOSYLATION; HYDROPHILICITY; PRIORITY JOURNAL; REACTION TIME; ROOM TEMPERATURE;

GLYCOSYLATION; IMIDAZOLES; IONIC LIQUIDS; TEMPERATURE; THIOGLYCOSIDES;

EID: 71649104525     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2009.09.034     Document Type: Article

References (36)

1. Varki A. Glycobiology 3 (1993) 97-130
2. Rudd P.M., Elliott T., Cresswell P., Wilson I.A., and Dwek R.A. Science 291 (2001) 2370-2376
3. Prescher J.A., and Bertozzi C.R. Nat. Chem. Biol. 1 (2005) 13-21
4. Sears P., and Wong C.H. Science 291 (2001) 2344-2350
5. Seeberger P.H., and Werz D.B. Nat. Rev. Drug Discovery 4 (2005) 751-763
6. Ernst B., Hart G., and Sinay P. Carbohydrates in Chemistry and Biology (2000), Wiley, Weinheim
7. Sheldon R. Chem. Commun. (2001) 2399-2407
8. Picquet M., Poinsot D., Stutzmann S., Tkatchenko I., Tommasi I., Wasserscheid P., and Zimmermann J. Top. Catal. 29 (2004) 139-143
9. Dominguez de Maria P. Angew. Chem., Int. Ed. 47 (2008) 6960-6968 and references therein
10. Murugesan S., Karst N., Islam T., Wiencek J.M., and Linhardt R.J. Synlett (2003) 1283-1286
11. Forsyth S.A., MacFarlane D.R., Thomson R.J., and von Itzstein M. Chem. Commun. (2002) 714-715
12. Rencurosi A., Lay L., Russo G., Caneva E., and Poletti L. J. Org. Chem. 70 (2005) 7765-7768
13. Sasaki K., Nagai H., Matsumura S., and Toshima K. Tetrahedron Lett. 44 (2003) 5605-5608
14. Murugesan S., and Linhardt R.J. Curr. Org. Synth. 2 (2005) 437-451
15. Galan M.C., Brunet C., and Fuensanta M. Tetrahedron Lett. 50 (2009) 442-445
16. Plaza P.G.J., Bhongade B.A., and Singh G. Synlett (2008) 2973-2976
17. Oscarson S. Carbohydrates in Chemistry and Biology Vol. 1 (2000), Wiley, Weinheim
18. Rencurosi A., Lay L., Russo G., Caneva E., and Poletti L. Carbohydr. Res. 341 (2006) 903-908
19. Baudequin C., Baudoux J., Levillain J., Cahard D., Gaumont A.C., and Plaquevent J.C. Tetrahedron: Asymmetry 14 (2003) 3081-3093
20. Gordon C.M. Appl. Catal., A 222 (2001) 101-117
21. El Seoud O.A., Koschella A., Fidale L.C., Dorn S., and Heinze T. Biomacromolecules 8 (2007) 2629-2647
22. Dieter K.M., Dymek C.J., Heimer N.E., Rovang J.W., and Wilkes J.S. J. Am. Chem. Soc. 110 (1988) 2722-2726
23. Mohile S.S., Potdar M.K., and Salunkhe M.M. Tetrahedron Lett. 44 (2003) 1255-1258
24. Hajipour A.R., Khazdooz L., and Ruoho A.E. Catal. Commun. 9 (2008) 89-96
25. Ferrier R.J., and Furneaux R.H. Carbohydr. Res. 52 (1976) 63-68
26. Zissis E., Clingman A.L., and Richtmyer N.K. Carbohydr. Res. 2 (1966) 461-469
27. Ohlsson J., and Magnusson G. Carbohydr. Res. 329 (2000) 49-55
28. Kreuzer M., and Thiem J. Carbohydr. Res. 149 (1986) 347-361
29. Fei Z., Zhao D., Geldbach T.J., Scopelliti R., and Dyson P.J. Chem. Eur. J. 10 (2004) 4886-4893
30. Patil M.L., and Sasai H. Chem. Rec. 8 (2008) 98-108
31. Bica K., Gmeiner G., Reichel C., Lendl B., and Gaertner P. Synth. Stuttgart (2007) 1333-1338
32. Bica K., and Gaertner P. Eur. J. Org. Chem. (2008) 3235-3250
33. Debdab M., Mongin F., and Bazureau J.P. Synthesis (2006) 4046-4052
34. Mootoo D.R., Konradsson P., Udodong U., and Fraserreid B. J. Am. Chem. Soc. 110 (1988) 5583-5584
35. Grayson E.J., Ward S.J., Hall A.L., Rendle P.M., Gamblin D.P., Batsanov A.S., and Davis B.G. J. Org. Chem. 70 (2005) 9740-9754
36. Chery F., Cassel S., Wessel H.P., and Rollin P. Eur. J. Org. Chem. (2002) 171-180