Microwave-assisted synthesis of a triazole-linked 3′-5′ dithymidine using click chemistry

Tetrahedron Letters

Volumn 49, Issue 6, 2008, Pages 1004-1007

  Lucas, Romain ^a   Neto, Virginie ^a   Hadj Bouazza, Amel ^a   Zerrouki, Rachida ^a   Granet, Robert ^a   Krausz, Pierre ^a   Champavier, Yves ^b  

^a UNIVERSITÉ DE LIMOGES   (France)

^b UNIVERSITY OF LIMOGES   (France)

Author keywords

Click chemistry; Dithymidine; Microwave; Selective chlorination

Indexed keywords

5' CHLORO 5' DEOXYTHYMIDINE; 5' TERT BUTYLDIMETHYLSILYLTHYMIDINE; THYMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHLORINATION; CYCLOADDITION; MICROWAVE IRRADIATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS;

EID: 37849008641     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.012     Document Type: Article

References (21)

1. Caruthers M.H. Science 230 (1985) 281-285
2. Uhlmann E., and Peyman A. Chem. Rev. 90 (1990) 543-584
3. Milligan J.F., Matteuci M.D., and Martin J.C. J. Med. Chem. 36 (1993) 1923-1937
4. De Mesmaeker A., Häner R., Martin P., Moser H.E., and Heinz E. Acc. Chem. Res. 28 (1995) 366-374
5. Sanghvi Y.S., and Cook P.D. In: Chu C.K., and Baker D.C. (Eds). Nucleosides and Nucleotides as Antitumor and Antiviral Agents (1993), Plenum Press, New York, US 311-324
6. Sanghvi Y.S., and Cook P.D. Carbohydrates. In: Sanghvi Y.S., and Cook P.D. (Eds). Carbohydrate Modifications in Antisense Research (1994), American Chemical Society, Washington, US 1-23
7. Rostovtsev V.V., Green L.G., Fokin V.V., and Sharpless K.B. Angew. Chem., Int. Ed. 41 (2002) 2596-2599
8. Helms B., Mynar J.L., Hawker C.J., Frechet J.M.J., and Sharpless K.B. J. Am. Chem. Soc. 126 (2004) 15020-15021
9. Wu P., Feldman A.K., Nugent A.K., Hawker C.J., Scheel A., Voit B., Pyun J., Frechet J.M.J., Sharpless K.B., and Fokin V.V. Angew. Chem., Int. Ed. 43 (2004) 2938-2954
10. Tornoe C.W., Christensen C., and Meldal M. J. Org. Chem. 67 (2002) 3057-3064
11. Colombeau L., Zerrouki R., Krausz P., and Champavier Y. Lett. Org. Chem. 2 (2005) 613-615
12. Roy V., Zerrouki R., and Krausz P. Nucleosides Nucleotides 24 (2005) 289-301
13. McCormick C.L., Dawsey T.R., and Newman K.J. Carbohydr. Res. 208 (1990) 183-191
14. Robins M.J., Dobozewski B., Nilsson B.L., and Peterson M.A. Nucleosides Nucleotides 19 (2000) 69-86
15. Corey E.J., and Vankateswarlu A. J. Am. Chem. Soc. 94 (1972) 6190-6191
16. Hanessian S., and Lavallee P. Can. J. Chem. 53 (1975) 2975-2977
17. Wu J.C., Xi Z., Gioeli C., and Chattopadhyaya J. Tetrahedron 47 (1991) 2237-2254
18. Huisgen R., Knorr R., Mobius L., and Szeimies G. Chem. Ber. 98 (1965) 4014-4021
19. Appukkutan P., Dehaen W., Fokin V.V., and Van der Eycken E. Org. Lett. 6 (2004) 4223-4225
20. Himo F., Lovell T., Hilgraf R., Rostovtsev V.V., Noodleman L., Sharpless K.B., and Fokin V.V. J. Am. Chem. Soc. 127 (2005) 210-216
21. Bock V.D., Hiemstra H., and Maarseveen J.H. Eur. J. Org. Chem. (2006) 51-68