Microwave-assisted synthesis of d-glucuronic acid derivatives using cost-effective solid acid catalysts

Tetrahedron Letters

Volumn 51, Issue 10, 2010, Pages 1356-1360

  Richel, Aurore ^a   Laurent, Pascal ^a   Wathelet, Bernard ^a   Wathelet, Jean Paul ^a   Paquot, Michel ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BETA DEXTRO GLUCOFURANOSIDURO 6,3 LACTONE; GLUCURONIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; COST EFFECTIVENESS ANALYSIS; HEATING; MICROWAVE RADIATION; SYNTHESIS;

EID: 75349098906     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.12.065     Document Type: Article

References (45)

1. Spahn-Langguth H., and Benet L.Z. Drug Metab. Rev. 24 (1992) 5-47
2. For relevant applications in the field of bioactive molecules design:. Stachulski A.V., and Jenkins G.J. Nat. Prod. Rep. 15 (1998) 173-186
3. Otto R.F., Bornscheuer U.T., Scheib H., Pleiss J., Syldatk C., and Schmid R.D. Biotechnol. Lett. 20 (1998) 1091-1094
4. Gautier C., Legault J., Rondeau S., and Pichette A. Tetrahedron Lett. 50 (2009) 988-991
5. For examples:. Doyle D., and Murphy P. Carbohydr. Res. 343 (2008) 2535-2544
6. Bergman K., Hilborn J., and Bowden T. Express Polym. Lett. 28 (2008) 553-559
7. Guiltot J., Benvegnu T., Legros N., and Plusquellec D. Langmuir 17 (2001) 613-618
8. Blecker C., Piccicuto S., Lognay G., Deroanne C., Marlier M., and Paquot M. J. Colloid Interface Sci. 247 (2008) 424-428
9. Berchel M., Lemiègre L., Jeftić J., and Benvegnu T. Tetrahedron Lett. 49 (2008) 4690-4692
10. Berchel M., Lemiègre L., Trépout S., Lambert O., Jeftić J., and Benvegnu T. Tetrahedron Lett. 49 (2008) 7419-7422
11. Timoshchuk V.A. Russ. Chem. Rev. 64 (1995) 675-703 and references therein
12. For examples of chemical synthesis:. Bertho J.-N., Ferrières V., and Plusquellec D. J. Chem. Soc., Chem. Commun. (1995) 1391-1393
13. Becker B., Barua A.B., and Olson J.A. Biochem. J. 314 (1996) 249-252
14. Ferrières V., Bertho J.-N., and Plusquellec D. Carbohydr. Res. 311 (1998) 25-35
15. Tosin M., and Murphy P.V. Org. Lett. 4 (2002) 3675-3678
16. Baddeley T.C., Davidson I.G., Skakle J.M.S., and Wardell J.L. J. Chem. Crystallogr. 33 (2003) 33-38
17. Poláková M., Pitt N., Tosin M., and Murphy P.V. Angew. Chem., Int. Ed. 43 (2004) 2518-2521
18. Gedye R., Smith F., Westaway K., Ali H., Baldisera L., Laberge L., and Roussel J. Tetrahedron Lett. 27 (1986) 279-282
19. Giguere R.J., Bray, T L., Duncan S.M., and Majetich G. Tetrahedron Lett. 27 (1986) 4945-4948
20. Kappe C.O. Angew. Chem., Int. Ed. 43 (2004) 6250-6284
21. Corsaro A., Chiacchio U., Pistarà V., and Romeo G. Curr. Org. Chem. 8 (2004) 511-538
22. Andrade M.M., Barros M.T., and Rodrigues P. Eur. J. Org. Chem. (2007) 3655-3668
23. Caddick S., and Fitzmaurice R. Tetrahedron 65 (2009) 3325-3355
24. Rat S., Mathiron D., Michaud P., Kovensky J., and Wadouachi A. Tetrahedron 63 (2007) 12424-12428
25. Wilson K., and Clark J.H. Pure Appl. Chem. 72 (2000) 1313-1319
26. Clark J.H. Acc. Chem. Res. 35 (2002) 791-797
27. In: Sheldon R.A., Arends I., and Hanefeld U. (Eds). Green Chemistry and Catalysis (2007), Wiley-VCH, Weinheim
28. Varma R.S. Green Chem. (1999) 43-55
29. Desai B., and Kappe C.O. Top. Curr. Chem. 242 (2004) 177-208 and references therein
30. Strauss C.R., and Varma R.S. Top. Curr. Chem. 266 (2006) 199-231
31. Salehi P., Zolfigol M.A., Shirini F., and Baghbanzadeh M. Curr. Org. Chem. 10 (2006) 2171-2189 and references therein
32. For selected examples of applications:. Rajput V.K., Roy B., and Mukhopadhyay B. Tetrahedron Lett. 47 (2006) 6987-6991
33. Khalafi-Nezhad A., Parhami A., Rad M.N.S., Zolfigol M.A., and Zare A. Tetrahedron Lett. 48 (2007) 5219-5222
34. Roy B., and Mukhopadhyay B. Tetrahedron Lett. 48 (2007) 3783-3787
35. Wu H., Shen Y., Fan L.-Y., Wan Y., Zhang P., Chen C.-F., and Wang W.-X. Tetrahedron 63 (2007) 2404-2408
36. Shaterian H.R., Ghashang M., and Feyzi M. Appl. Catal., A 345 (2008) 128-133
37. For selected examples:. Kozhevnikov V., Kloetstra K.R., Sinnema A., Zandbergen H.W., and van Bekkum H. J. Mol. Catal. A: Chem. 114 (1996) 287-298
38. Blsaco T., Corma A., Martínez A., and Martínez-Escolano P. J. Catal. 177 (1998) 306-313
39. Clark J.H., and Rhodes C.N. Clean Synthesis using Porous Inorganic Solid Acids and Supported Reagents (2000), Royal Society of Chemistry, Cambridge
40. Smith K., Fry C.V., and Tzimas M. In: Clark J.H. (Ed). Chemistry of Waste Minimization (1995), Blackie Academic, London 86-115
41. Perin G., Álvaro G., Westphal E., Viana L.H., Jacob R.G., Lenardão E.J., and D'Oca M.G.M. Fuel 87 (2008) 2838-2841
42. 60 and silica-supported Keggin type heteropolyacid. After preparation, each catalytic system was dried for 24 h in static air at 120 °C and stored in a desiccator under vacuum.
43. Kogelbauer A., Vassena D., Prins R., and Armor J.N. Catal. Today 55 (2000) 151-160
44. 60 was stirred together with methanol, under microwave heating at 85 °C for 10 min.
45. 2).