Evaluation of bis-triphenylphosphano-copper(I)-butyrate (C 3H 7COOCu(PPh 3) 2) as catalyst for the synthesis of 1-glycopyranosyl-4-substituted-1,2,3-triazoles

Carbohydrate Research

Volumn 351, Issue , 2012, Pages 42-48

  Bokor, Éva ^a   Koppány, Csenge ^a   Gonda, Zsombor ^b   Novák, Zoltán ^b   Somsák, László ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

1 Glycopyranosyl 1,2,3 triazole; Azide alkyne cycloaddition; Glycopyranosyl azide

Indexed keywords

1-GLYCOPYRANOSYL-1,2,3- TRIAZOLE; ACID SYSTEMS; AZIDE-ALKYNE CYCLOADDITION; GLYCOPYRANOSYL; GLYCOSYL AZIDES;

ACETYLENE; CATALYSTS; COPPER; NITROGEN COMPOUNDS;

VOLATILE FATTY ACIDS;

1 (2' ACETAMIDO 2' DEOXY 3',4',6' TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 (2 NAPHTHYL) 1,2,3 TRIAZOLE; 1 (2' ACETAMIDO 2' DEOXY 3',4',6' TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 PHENYL 1,2,3 TRIAZOLE; 1 (2' ACETAMIDO 2' DEOXY 3',4',6' TRI O ACETYL BETA DEXTRO XYLOPYRANOSYL) 1,2,3 TRIAZOLE; 1 (2' DEOXY 2' PHTALIMIDO 3',4',6' TRI O ACETYL ALPHA DEXTRO GLUCOPYRANOSYL) 4 PHENYL 1,2,3 TRIAZOLE; 1 (2' DEOXY 2' PHTALIMIDO 3',4',6' TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 (2 NAPHTHYL) 1,2,3 TRIAZOLE; 1 (2' DEOXY 2' PHTALIMIDO 3',4',6' TRI O ACETYL BETA DEXTRO GLUCOPYRANOSYL) 4 PHENYL 1,2,3 TRIAZOLE; 4 (2 NAPHTHYL) 1 (2',3',4' TRI O ACETYL BETA DEXTRO XYLOPYRANOSYL) 1,2,3 TRIAZOLE; 4 ACETOXYMETHYL 1 (2',3',4' TRI O ACETYL BETA DEXTRO XYLOPYRANOSYL) 1,2,3 TRIAZOLE; 4 ACETOXYMETHYL 1 (2',3',4',6' TETRA O ACETYL ALPHA ARABINOPYRANOSYL) 1,2,3 TRIAZOLE; 4 ACETOXYMETHYL 1 (2',3',4',6' TETRA O ACETYL BETA ARABINOPYRANOSYL) 1,2,3 TRIAZOLE; 4 ACETOXYMETHYL 1 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 1,2,3 TRIAZOLE; 4 PHENYL 1 (2',3',4' TRI O ACETYL BETA ARABINOPYRANOSYL) 1,2,3 TRIAZOLE; 4 PHENYL 1 (2',3',4' TRI O ACETYL BETA DEXTRO XYLOPYRANOSYL) 1,2,3 TRIAZOLE; 4 PHENYL 1 (2',3',4',6' TETRA O ACETYL ALPHA ARABINOPYRANOSYL) 1,2,3 TRIAZOLE; 4 PHENYL 1 (2',3',4',6' TETRA O ACETYL BETA DEXTRO GALACTOPYRANOSYL) 1,2,3 TRIAZOLE; ALKYNE DERIVATIVE; ASCORBIC ACID; AZIDE; BIS TRIPHENYLPHOSPHANO COPPER BUTYRATE; BUTYRIC ACID DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; PRIORITY JOURNAL; SUBSTITUTION REACTION;

CATALYSIS; CHEMISTRY TECHNIQUES, SYNTHETIC; COORDINATION COMPLEXES; TRIAZOLES;

EID: 84858069275     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.01.004     Document Type: Article

References (35)

1. M. Meldal, and C.W. Tornoe Chem. Rev. 108 2008 2952 3015
2. S.G. Agalave, S.R. Maujan, and V.S. Pore Chem. Asian J. 6 2011 2696 2718
3. S. Dedola, S.A. Nepogodiev, and R.A. Field Org. Biomol. Chem. 5 2007 1006 1017
4. A. Dondoni Chem. Asian J. 2 2007 700 708
5. F. Santoyo Gonzalez, and F. Hernandez-Mateo Top. Heterocycl. Chem. 7 2007 133 177
6. V. Aragao-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475 9492
7. R.A. Akula, D.P. Temelkoff, N.D. Artis, and P. Norris Heterocycles 63 2004 2719 2725
8. B.L. Wilkinson, L.F. Bornaghi, S.-A. Poulsen, and T.A. Houston Tetrahedron 62 2006 8115 8125
9. B. Kuberan, M. Ethirajan, X.V. Victor, V. Tran, K. Nguyen, and A. Do Chembiochem 9 2008 198 200
10. I. Carvalho, P. Andrade, V.L. Campo, P.M.M. Guedes, R. Sesti-Costa, J.S. Silva, S. Schenkman, S. Dedola, L. Hill, M. Rejzek, S.A. Nepogodiev, and R.A. Field Bioorg. Med. Chem. 18 2010 2412 2427
11. S. Dedola, D.L. Hughes, S.A. Nepogodiev, M. Rejzek, and R.A. Field Carbohydr. Res. 345 2010 1123 1134
12. T.H. Li, L.N. Guo, Y. Zhang, J.J. Wang, Z.H. Li, L. Lin, Z.X. Zhang, L. Li, J.P. Lin, W. Zhao, J. Li, and P.G. Wang Carbohydr. Res. 346 2011 1083 1092
13. K.J.V. Paul, and D. Loganathan Tetrahedron Lett. 49 2008 6356 6359
14. B.H.M. Kuijpers, S. Groothuys, A.B.R. Keereweer, P.J.L.M. Quaedflieg, R.H. Blaauw, F.L.v. Delft, and F.P.J.T. Rutjes Org. Lett. 6 2004 3123 3126
15. J.V. dos Anjos, D. Sinou, S.J. de Melo, and R.M. Srivastava Synthesis 2007 2647 2652
16. S. Chittaboina, F. Xie, and Q. Wang Tetrahedron Lett. 46 2005 2331 2336
17. D. Ermolat'ev, W. Dehaen, and E. Van der Eycken QSAR Comb. Sci. 23 2004 915 918
18. A. Baron, Y. Bleriot, M. Sollogoub, and B. Vauzeilles Org. Biomol. Chem. 6 2008 1898 1901
19. L.L. Rossi, and A. Basu Bioorg. Med. Chem. Lett. 15 2005 3596 3599
20. S. Groothuys, B.H.M. Kuijpers, P.J.L.M. Quaedflieg, H.C.P.F. Roelen, R.W. Wiertz, R.H. Blaauw, F.L.v. Delft, and F.P.J.T. Rutjes Synthesis 2006 3146 3152
21. N. Pietrzik, C. Schips, and T. Ziegler Synthesis 2008 519 526
22. S.A. Nepogodiev, S. Dedola, L. Marmuse, M.T.d. Oliveira, and R.A. Field Carbohydr. Res. 342 2007 529 540
23. S. Lal, and S. Diez-Gonzalez J. Org. Chem. 76 2011 2367 2373
24. É. Bokor, T. Docsa, P. Gergely, and L. Somsák Bioorg. Med. Chem. 18 2010 1171 1180
25. E.D. Chrysina, É. Bokor, K.-M. Alexacou, M.-D. Charavgi, G.N. Oikonomakos, S.E. Zographos, D.D. Leonidas, N.G. Oikonomakos, and L. Somsák Tetrahedron: Asymmetry 20 2009 733 740
26. W.S. Horne, M.K. Yadav, C.D. Stout, and M.R. Ghadiri J. Am. Chem. Soc. 126 2004 15366 15367
27. G. Appendino, S. Bacchiega, A. Minassi, M.G. Cascio, L. De Petrocellis, and V. Di Marzo Angew. Chem., Int. Ed. 46 2007 9312 9315
28. Y.L. Angell, and K. Burgess Chem. Soc. Rev. 36 2007 1674 1689
29. Z. Gonda, and Z. Novák Dalton Trans. 39 2010 726 729
30. A. Gangjee, J.M. Yu, and R.L. Kisliuk J. Heterocycl. Chem. 39 2002 833 840
31. L. Szilágyi, and Z. Györgydeák Carbohydr. Res. 143 1985 21 41
32. K. Czifrák, L. Kovács, K.E. Kövér, and L. Somsák Carbohydr. Res. 340 2005 2328 2334
33. H. Paulsen, Z. Györgydeák, and M. Friedmann Chem. Ber. 107 1974 1568 1578
34. Z. Györgydeák, and J. Thiem Adv. Carbohydr. Chem. Biochem. 60 2006 103 182
35. Z. Györgydeák, and L. Szilágyi Liebigs Ann. 1987 235 241