A simple and useful synthetic protocol for selective deprotection of tert-butyldimethylsilyl (TBS) ethers

European Journal of Organic Chemistry

Volumn , Issue 10, 2004, Pages 2198-2204

  Khan, Abu T ^a   Ghosh, Subrata ^a   Choudhury, Lokman H ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Deprotection; Ethers; Protecting groups; Synthesis design

Indexed keywords

ACETONYLTRIPHENYLPHOSPHONIUM BROMIDE; ETHER DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BROMINATION; CATALYSIS; CATALYST; DEPROTECTION REACTION; ROOM TEMPERATURE; SYNTHESIS;

EID: 4544337310     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200400031     Document Type: Article

References (42)

1. E. J. Corey, A. Venkateswarlu, J. Am. Chem. Soc. 1972, 94, 6190-6191.
2. T. W. Greene, P. G. M. Wuts, Protective Groups in Organic Synthesis, 3rd ed., John Wiley & Sons, Inc., New York, 1999, pp. 127-144.
3. S. Hanessian, P. Lavallee, Can. J. Chem. 1975, 53, 2975.
4. J. H. Clark, Chem. Rev. 1980, 80, 429-452.
5. [5a] D. R. Kelly, S. M. Roberts, R. F. Newton, Synth. Commun. 1979, 9, 295.
6. [5b] E. W. Collington, H. Finch, I. J. Smith, Tetrahedron Lett. 1985, 26, 681-684.
7. [5c] S. J. Shimshock, R. E. Watermire, P. Deshong, J. Am. Chem. Soc. 1991, 113, 8791-8796.
8. [5d] W. Zhang, M. J. Robins, Tetrahedron Lett. 1992, 33, 1177-1180.
9. [5e] E. J. Corey, K. Y. Yi, Tetrahedron Lett. 1992, 33, 2289-2290.
10. [5f] K. S. Ramasamy, D. Averett, Synlett 1999, 709-712.
11. [5g] B. W. Metcalf, J. P. Burkhart, K. Jund, Tetrahedron Lett. 1980, 21, 35-36.
12. [5h] B. C. Ranu, U. Jana, A. Majee, Tetrahedron Lett. 1999, 40, 1985-1988.
13. [6a] G. Bartoli, M. Bosco, E. Marcantoni, L. Sambri, E. Torregiani, Synlett 1998, 209-211.
14. [6b] S. V. Ankala, G. Fenteany, Tetrahedron Lett. 2002, 43, 4729-4732.
15. [6c] J. Farras, C. Serra, J. Vilarrasa, Tetrahedron Lett. 1998, 39, 327-330.
16. [6d] P. A. Grieco, C. J. Markworth, Tetrahedron Lett. 1999, 40, 665-666.
17. [6e] G. V. M. Sharma, B. Srinivas, P. R. Krishna, Tetrahedron Lett. 2003, 44, 4689-4691.
18. [6d] A. T. Khan, E. J. Mondal, Synlett 2003, 694-698.
19. [7a] R. Hunter, W. Hinz, P. Richards, Tetrahedron Lett. 1999, 40, 3643-3646.
20. [7b] T. Oriyama, Y. Kobayashi, K. Noda, Synlett 1998, 1047-1048.
21. [7c] B. H. Lipshutz, J. Keith, Tetrahedron Lett. 1998, 39, 2495-2498.
22. [7d] G. Sabitha, M. Syamala, J. S. Yadav, Org. Lett. 1999, 1, 1701-1703.
23. [7e] I. Paterson, C. J. Cowden, V. S. Rahn, M. D. Woodrow, Synlett 1998, 915-917.
24. [7f] Y. J. Jeong, J. H. Lee, E. S. Park, C. M. Yoon, J. Chem. Soc., Perkin Trans. 1 2002, 1223-1225.
25. [7g] K. Oyama, T. Kondo, Org. Lett. 2003, 5, 209-212.
26. [7h] Z. Jiang, Y. Wang, Tetrahedron Lett. 2003, 44, 3859-3861.
27. [8a] A. D. Lee, H. Yeh, J. Shie, Tetrahedron Lett. 1998, 39, 5249-5252.
28. [8b] J. S. Bajwa, J. Vivelo, J. Slade, O. Repic, T. Blacklock, Tetrahedron Lett. 2000, 41, 6021-6024.
29. [8c] T. Oriyama, M. Oda, J. Gono, G Koga, Tetrahedron Lett. 1994, 35, 2027-2030.
30. [8d] R. Gopinath, B. K. Patel, Org. Lett. 2000, 2, 4177-4180.
31. [8e] M. T. Barros, C. D. Maycock, C. Thomassigny, Synlett 2001, 1146-1148.
32. [8f] K. P. R. Kartha, R. A. Field, Synlett 1999, 311-312.
33. [9a] E. Mondal, P. R. Sahu, G. Bose, A. T. Khan, Tetrahedron Lett. 2002, 43, 2843-2846.
34. [9b] E. Mondal, P. R. Sahu, A. T. Khan, Synlett 2002, 463-467.
35. [9c] A. T. Khan, E. Mondal, P. R. Sahu, Synlett 2003, 377-381.
36. [10a] B. E. Maryanoff, A. B. Reitz, Chem. Rev. 1989, 89, 863.
37. [10b] Y.-S. Hon, C.-F. Lee, Tetrahedron Lett. 1999, 40, 2389-2392.
38. [10c] Y.-S. Hon, C.-F. Lee, R.-J. Chenn, P.-H. Szu, Tetrahedron 2001, 57, 5991-6001.
39. [10d] Y.-S. Hon, C.-F. Lee, Tetrahedron 2001, 57, 6181-6188.
40. [11a] A. T. Khan, E. Mondal, B. M. Borah, S. Ghosh, Eur. J. Org. Chem. 2003, 4113-4117.
41. [11b] A. T. Khan, E. Mondal, S. Ghosh, S. Islam, Eur. J. Org. Chem. 2004, in press.
42. 1H NMR spectra of the products were compared with the Aldrich Spectral Library.