A highly efficient and useful synthetic protocol for the cleavage of tert-butyldimethylsilyl (TBS) ethers using a catalytic amount of acetyl chloride in dry methanol

Synlett

Volumn , Issue 5, 2003, Pages 694-698

  Khan, Abu T ^a   Mondal, Ejabul ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Acetyl chloride; Deprotection; tert butyldimethylsilyl (TBS) ethers; tert butyldiphenylsilyl (TBDPS) ethers

Indexed keywords

ACETIC ACID DERIVATIVE; CHLORINE DERIVATIVE; ETHER DERIVATIVE; HYDROXYL GROUP; METHANOL;

ACETYLATION; ARTICLE; CATALYST; CHLORINATION; DEPROTECTION REACTION; PRODUCTIVITY; ROOM TEMPERATURE; SYNTHESIS;

EID: 0037263570     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-38360     Document Type: Article

References (38)

1. Corey, E. J.; Venkateswarlu, A. J. Am. Chem. Soc. 1972, 94, 6190.
2. Hanessian, S.; Lavallee, P. Can. J. Chem. 1975, 53, 2975.
3. (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley and Sons: New York, 1999, 127-144.
4. (b) Clark, J. H. Chem. Rev. 1980, 80, 429.
5. (a) Kelly, D. R.; Roberts, S. M.; Newton, R. F. Synth. Commun. 1979, 9, 295.
6. (b) Collington, E. W.; Finch, H.; Smith, I. J. Tetrahedron Lett. 1985, 26, 681.
7. (c) Shimshock, S. J.; Watermire, R. E.; Deshong, P. J. Am. Chem. Soc. 1991, 113, 8791.
8. (d) Zhang, W.; Robins, M. J. Tetrahedron Lett. 1992, 33, 1177.
9. (e) Corey, E. J.; Yi, K. Y. Tetrahedron Lett. 1992, 33, 2289.
10. (f) Ramasamy, K. S.; Averett, D. Synlett 1999, 709.
11. (g) Metcalf, B. W.; Burkhart, J. P.; Jund, K. Tetrahedron Lett. 1980, 21, 35.
12. (h) Ranu, B. C.; Jana, U.; Majee, A. Tetrahedron Lett. 1999, 40, 1985.
13. (a) Lee, A. S.; Yeh, H.; Shie, J. Tetrahedron Lett. 1998, 39, 5249.
14. (b) Bajwa, J. S.; Vivelo, J.; Slade, J.; Repi, O.; Blacklock, T. Tetrahedron Lett. 2000, 41, 6021.
15. (c) Oriyama, T.; Oda, M.; Gono, J.; Koga, G. Tetrahedron Lett. 1994, 35, 2027.
16. (d) Gopinath, R.; Patel, B. K. Org. Lett. 2000, 2, 4177.
17. (e) Barros, M. T.; Maycock, C. D.; Thomassigny, C. Synlett 2001, 1146.
18. (f) Kartha, K. P. R.; Field, R. A. Synlett 1999, 311.
19. (a) Bartoli, G.; Bosco, M.; Marcantoni, E.; Sambri, L.; Torregiani, E. Synlett 1998, 209.
20. (b) Ankala, S. V.; Fenteany, G. Tetrahedron Lett. 2002, 43, 4729.
21. (c) Farras, J.; Serra, C.; Vilarrasa, J. Tetrahedron Lett. 1998, 39, 327.
22. (d) Grieco, P. A.; Markworth, C. J. Tetrahedron Lett. 1999, 40, 665.
23. (a) Hunter, R.; Hinz, W.; Richards, P. Tetrahedron Lett. 1999, 40, 3643.
24. (b) Oriyama, T.; Kobayashi, Y.; Noda, K. Synlett 1998, 1047.
25. (c) Lipshutz, B. H.; Keith, J. Tetrahedron Lett. 1998, 39, 2495.
26. (d) Sabitha, G.; Syamala, M.; Yadav, J. S. Org. Lett. 1999, 1, 1701.
27. (e) Paterson, I.; Cowden, C. J.; Rahn, V. S.; Woodrow, M. D. Synlett 1998, 915.
28. (a) Mondal, E.; Bose, G.; Khan, A. T. Synlett 2001, 785.
29. (b) Mondal, E.; Bose, G.; Sahu, P. R.; Khan, A. T. Chem. Lett. 2001, 1158.
30. (c) Khan, A. T.; Boruwa, J.; Mondal, E.; Bose, G. Indian J. Chem, Sect. B 2001, 40, 1039.
31. (d) Mondal, E.; Sahu, P. R.; Bose, G.; Khan, A. T. Tetrahedron Lett. 2002, 43, 2843.
32. (e) Mondal, E.; Sahu, P. R.; Khan, A. T. Synlett 2002, 463.
33. (f) Mondal, E.; Sahu, P. R.; Bose, G.; Khan, A. T. J. Chem. Soc., Perkin Trans. 1 2002, 1026.
34. (g) Khan, A. T.; Mondal, E.; Sahu, P. R.; Islam, S. Tetrahedron Lett. 2003, 44, 919.
35. (h) Khan, A. T.; Mondal, E.; Sahu, P. R. Synlett 2003, 377.
36. Khan, A. T.; Mondal, E. unpublished results.
37. 4) and concentrated in vacuo to give a 'crude' residue, which was purified on silica gel column chromatography. The final desired products were obtained in good to excellent yields.
38. 6: C, 55.37; H, 7.74. Found: C, 55.48; H, 7.69.