Addressing the scope of the azide-nitrile cycloaddition in glycoconjugate chemistry. The assembly of C-glycoclusters on a calix[4]arene scaffold through tetrazole spacers

Tetrahedron

Volumn 63, Issue 27, 2007, Pages 6339-6345

  Dondoni, Alessandro ^a   Marra, Alberto ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

1,3 Dipolar cycloaddition; C glycoside; Glycocluster; Sugar azide; Tetrazole

Indexed keywords

AZIDE; CALIXARENE; CYANIDE; GLYCOCONJUGATE; GLYCOSIDE; NITRILE; TETRAZOLE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLOADDITION; DRUG SYNTHESIS; PRIORITY JOURNAL;

EID: 34249073722     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.03.045     Document Type: Article

References (41)

1. Huisgen R., Szeimies G., and Möbius L. Chem. Ber. 100 (1967) 2494-2507
2. Huisgen R. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), Wiley, New York, NY 1-176
3. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
4. Tornøe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
5. Bioconjugate chemistry:
6. Breinbauer R., and Köhn M. ChemBioChem 4 (2003) 1147-1149
7. Pérez-Balderas F., Ortega-Muñoz M., Morales-Sanfrutos J., Hernandez-Mateo F., Calvo-Flores F.G., Calvo-Asin J.A., Isac-Garcia J., and Santoyo-Gonzales F. Org. Lett. 5 (2003) 1951-1954
8. van Maarseveen J.H., and Back J.W. Angew. Chem., Int. Ed. 42 (2003) 5926-5928
9. Zhu X., and Schmidt R.R. J. Org. Chem. 69 (2004) 1081-1085
10. Dondoni A., and Giovannini P.P. Org. Lett. 6 (2004) 2929-2932
11. Kuijpers B.H.M., Groothuys S., Keereweer A.R., Quaedflieg P.J.L.M., Blaauw R.H., van Delft F.L., and Rutjes F.P.J.T. Org. Lett. 6 (2004) 3123-3126
12. Dorner S., and Westermann B. Chem. Commun. (2005) 2852-2854
13. Punna S., Kuzelka J., Wang Q., and Finn M.G. Angew. Chem., Int. Ed. 44 (2005) 2215-2220
14. Weller R.L., and Rajski S.R. Org. Lett. 7 (2005) 2141-2144
15. Jang H., Fafarman A., Holub J.M., and Kirshenbaum K. Org. Lett. 7 (2005) 1951-1954
16. Wong C.-H. J. Org. Chem. 70 (2005) 4219-4225
17. Bodine K.D., Gin D.Y., and Gin M.S. Org. Lett. 7 (2005) 4479-4482
18. Chittaboina S., Xie F., and Wang Q. Tetrahedron Lett. 46 (2005) 2331-2336
19. Cheshev P., Marra A., and Dondoni A. Org. Biomol. Chem. 4 (2006) 3225-3227
20. Drug discovery:
21. Kolb H.C., and Sharpless K.B. Drug Discov. Today 8 (2003) 1128-1137
22. Cavalli S., Tipton A.R., Overhand M., and Kros A. Chem. Commun. (2006) 3193-3195
23. Resin and dendrimer synthesis:
24. Lober S., Rodriguez-Loaiza P., and Gmeiner P. Org. Lett. 5 (2003) 1753-1755
25. Wu P., Feldman A.K., Nugent A.K., Hawker C.J., Scheel A., Voit B., Pyun J., Fréchet J.M.J., Sharpless K.B., and Fokin V.V. Angew. Chem., Int. Ed. 43 (2004) 3928-3932
26. Rozkiewicz D.I., Janczewski D., Verboom W., Ravoo B.J., and Reinhoudt D.N. Angew. Chem., Int. Ed. 45 (2006) 5292-5296
27. Butler R.N. In: Katritzky A.R., Rees C.W., and Scriven E.F.V. (Eds). Comprehensive Heterocyclic Chemistry Vol. 4 (1966), Pergamon, Oxford, UK
28. Benson F.R. In: Elderfield R.C. (Ed). Heterocyclic Compounds Vol. 4 (1966), John Wiley & Sons, New York, NY
29. Carpenter W.R. J. Org. Chem. 27 (1962) 2085-2088
30. Quast H., and Bieber L. Tetrahedron Lett. 18 (1976) 1485-1486
31. Demko Z.P., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2110-2113
32. Zhang L., Chen X., Xue P., Sun H.H.Y., Williams I.D., Sharpless K.B., Fokin V.V., and Jia G. J. Am. Chem. Soc. 127 (2005) 15998-15999
33. Dondoni A., and Marra A. J. Org. Chem. 71 (2006) 7546-7557
34. Lee Y.C., Lee R.T., Rice K., Ichikawa Y., and Wong T.-C. Pure Appl. Chem. 63 (1991) 499-506
35. Lee Y.C., and Lee R.T. Acc. Chem. Res. 28 (1995) 321-326
36. Sigal G.B., Mammen M., Dahmann G., and Whitesides G.M. J. Am. Chem. Soc. 118 (1996) 3789-3800
37. Lundquist J.J., and Toone E.J. Chem. Rev. 102 (2002) 555-578
38. Dondoni A., Massi A., Sabbatini S., and Bertolasi V. J. Org. Chem. 67 (2002) 6979-6994
39. Dondoni A., Kleban M., Hu X., Marra A., and Banks H.D. J. Org. Chem. 67 (2002) 4722-4733
40. Armarego W.L.F., and Chai C.L.L. Purification of Laboratory Chemicals. 5th ed. (2003), Butterworth-Heinemann, Amsterdam
41. Still W.C., Kahn M., and Mitra A. J. Org. Chem. 43 (1978) 2923-2925