Synthesis of 1,2,3-triazolylpyranosides through click chemistry reaction

Tetrahedron Letters

Volumn 53, Issue 14, 2012, Pages 1742-1747

  Stefani, Hélio A ^a   Silva, Nathália C S ^a   Manarin, Flávia ^a   Lüdtke, Diogo S ^b   Zukerman Schpector, Julio ^c   Madureira, Lucas Sousa ^c   Tiekink, Edward R T ^d  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^c FEDERAL UNIVERSITY OF SÃO CARLOS   (Brazil)

^d UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

1,2,3 Triazole; Click chemistry; Cycloaddition; d Glucal; Selenosugars

Indexed keywords

ALKYNE; AZIDE; C GLYCOSYL 1,2,3 TRIAZOLE DERIVATIVE; COPPER; GLYCOSIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHIRALITY; CYCLOADDITION; DRUG SYNTHESIS; ULTRASOUND;

EID: 84857786565     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.01.102     Document Type: Article

References (52)

1. D.E. Levy, and C. Tang The Chemistry of C-Glycosides 1995 Pergamon Oxford, UK
2. G.E. Ritchie, B.E. Moffatt, R.B. Sim, B.P. Morgan, R.A. Dwek, and P.M. Rudd Chem. Rev. 102 2002 305
3. T. Nakata Chem. Rev. 105 2005 4314
4. K.C. Nicolaou, M.O. Frederick, and R.J. Aversa Angew. Chem., Int. Ed. 47 2008 7182
5. L. Somsak Chem. Rev. 101 2001 81
6. M.H.D. Postema Tetrahedron 48 1992 8545
7. K.C. Nicolaou, and H.J. Mitchell Angew. Chem., Int. Ed. 40 2001 1576
8. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596
9. C.W. Tornøe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057
10. K.D. Hanni, and D.A. Leigh Chem. Soc. Rev. 39 2010 1240
11. P.L. Golas, and K. Matyjaszewski Chem. Soc. Rev. 39 2010 1338
12. F. Amblard, J.H. Cho, and R.F. Schinazi Chem. Rev. 109 2009 4207
13. P.M.E. Gramlich, C.T. Wirges, A. Manetto, and T. Carell Angew. Chem., Int. Ed. 47 2008 8350
14. F. Seela, and S.S. Pujari Bioconjugate Chem. 21 2010 1629
15. K. Chen, and X. Chen Curr. Top. Med. Chem. 10 2010 1227
16. C. Wangler, R. Schirrmacher, P. Bartenstein, and B. Wangler Curr. Med. Chem. 17 2010 1092
17. A.D. Moorhouse, and J.E. Moses Chem. Med. Chem. 3 2008 715
18. N. Uhlig, and C.C. Li Chem. Sci. 2 2011 1241
19. M.D. Best Biochemistry 48 2009 6571
20. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004
21. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128
22. M. Meldal, and C.W. Tornøe Chem. Rev. 108 2008 2952
23. J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302
24. F.C. Silva, M.C.B.V. Souza, I.I.P. Frugulhetti, H.C. Castro, S.L.O. Souza, T.M.L. Souza, D.Q. Rodrigues, A.M.T. Souza, P.A. Abreu, F. Passamani, C.R. Rodrigues, and V.F. Ferreira Eur. J. Med. Chem. 44 2009 373
25. L.S. Kallander, Q. Lu, W. Chen, T. Tomaszek, G. Yang, D. Tew, T.D. Meek, G.A. Hofmann, C.K. Schulz-Pritchard, W.W. Smith, C.A. Janson, M.D. Ryan, G.F. Zhang, K.O. Johanson, R.B. Kirkpatrick, T.F. Ho, P.W. Fisher, M.R. Mattern, R.K. Johnson, M.J. Hansbury, J.D. Winkler, K.W. Ward, D.F. Veber, and S.K. Thompson J. Med. Chem. 48 2005 5644
26. X.L. Wang, K. Wan, and C.H. Zhou Eur. J. Med. Chem. 45 2010 4631
27. M.S. Costa, N. Boechat, E.A. Rangel, F.C. Silva, A.M.T. Souza, C.R. Rodrigues, H.C. Castro, I.N. Junior, M.C.S. Loureno, S.M.S.V. Wardell, and V.F. Ferreira Bioorg. Med. Chem. 14 2006 8644
28. T.D. Heightman, A. Vasella, K.E. Tsitsanou, S.E. Zographos, V.T. Skamnaki, and N.G. Oikonomakos Helv. Chim. Acta 81 1998 853
29. T.M. Krulle, C.D. Fuente, L. Pickering, R.T. Aplin, K.E. Tsitsanou, S.E. Zographos, N.G. Oikonomakos, R.J. Nash, R.C. Griffiths, and G.W. Fleet Tetrahedron: Asymmetry 8 1997 3807
30. V.D. Bock, D. Speijer, H. Hiemstra, and J.H. van Maarseveen Org. Biomol. Chem. 5 2007 971
31. A. Adibekian, B.R. Martin, C. Wang, K.L. Hsu, D.A. Bachovchin, S. Niessen, H. Hoover, and B.F. Cravatt Nature Chem. Biol. 7 2011 469
32. Recent reviews, see: S. Dedola, S.A. Nepogodiev, and R.A. Field Org. Biomol. Chem. 5 2007 1006
33. F. Santoyo-Gonzalez, and F. Hernandez-Mateo Chem. Soc. Rev. 38 2009 3449
34. V. Aragão-Leoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475
35. A.S. Vieira, P.F. Fiorante, T.L.S. Hough, F.P. Ferreira, D.S. Lüdtke, and H.A. Stefani Org. Lett. 10 2008 5215
36. V. Fiandanese, D. Bottalico, G. Marchese, A. Punzi, and F. Capuzzolo Tetrahedron 65 2009 10573
37. F.V. Singh, and H.A. Stefani Tetrahedron Lett. 51 2010 863
38. F.V. Singh, and H.A. Stefani Synlett 2008 3221
39. F.V. Singh, M. Weber, R.C. Guadagnin, and H.A. Stefani Synlett 2008 1889
40. R. Cella, and H.A. Stefani Tetrahedron 65 2009 2619
41. H.A. Stefani, A.S. Vieira, M.F.Z.J. Amaral, and L. Cooper Tetrahedron Lett. 52 2011 4256
42. P. Cintas, G. Palmisano, and G. Cravotto Ultrasonics Sonochem. 18 2011 836 and references therein.
43. J. Zukerman-Schpector, H.A. Stefani, N.C.S. Silva, S.W. Ngc, and E.R.T. Tiekink Acta Cryst. E67 2011 o2757
44. H.D. Flack Acta Cryst. A39 1983 876
45. J.N. Payette, and H. Yamamoto J. Am. Chem. Soc. 130 2008 12276
46. K.B. Hong, M.G. Donahue, and J.N. Johnston J. Am. Chem. Soc. 130 2008 2323
47. S. Sun, and P. Wu J. Phys. Chem. A 114 2010 8331
48. For reviews, see: G. Mugesh, W. du Mont, and H. Sies Chem. Rev. 101 2001 2125
49. C.W. Nogueira, G. Zeni, and J.B.T. Rocha Chem. Rev. 104 2004 6255
50. E.E. Alberto, V. Nascimento, and A.L. Braga J. Braz. Chem. Soc. 21 2010 2032
51. H.C. Braga, A.D. Wouters, F.B. Zerillo, and D.S. Lüdtke Carbohydr. Res. 345 2010 2328
52. H.C. Braga, H.A. Stefani, M.W. Paixão, F.W. Santos, and D.S. Lüdtke Tetrahedron 66 2010 3441