Trifluoroacetic acid-mediated cleavage of a triethylsilyl protecting group: Application in the final step of the semisynthetic route to paclitaxel (Taxol)

Organic Process Research and Development

Volumn 7, Issue 1, 2003, Pages 25-27

  Singh, Ambarish K ^a   Weaver, Raymond E ^a   Powers, Gerald L ^a   Rosso, Victor W ^a   Wei, Chenkou ^a   Lust, David A ^a   Kotnis, Atul S ^a   Comezoglu, F Taha ^a   Liu, Mark ^a   Bembenek, Kenneth S ^a   Phan, Bich D ^a   Vanyo, Dale J ^a   Davies, Merrill L ^a   Mathew, Rachel ^a   Palaniswamy, Venkatapuram A ^a   Li, Wen Sen ^a   Gadamsetti, Kumar ^a   Spagnuolo, Ciro J ^a   Winter, William J ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; HYDROXYL GROUP; PACLITAXEL; SILICON DERIVATIVE; TRIFLUOROACETIC ACID;

AQUEOUS SOLUTION; ARTICLE; DEPROTECTION REACTION; DRUG IMPURITY; DRUG QUALITY; DRUG SYNTHESIS; METHODOLOGY;

EID: 0037283350     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op020221k     Document Type: Article

References (8)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325.
2. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 277, 655.
3. (a) Holton, R. A. Abstracts of Papers, 203rd National Meeting of the American Chemical Society, San Francisco, CA; American Chemical Society: Washington, DC, 1991; ORGN 0355.
4. (b) Holton, R. A. U.S. Patents 5,015,744, 1991 and 5,136,060, 1992.
5. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; Wiley-Interscience: New York, 1999.
6. le Chatelier's principle states that, "if, to a system in equilibrium, a stress is applied, the system will react so as to relieve the stress". (a) Thomsen, V. E. J. Chem. Educ. 2000, 77, 173. (b) Raviolo, A. J. Chem. Educ. 2001, 78, 629.
7. le Chatelier's principle states that, "if, to a system in equilibrium, a stress is applied, the system will react so as to relieve the stress". (a) Thomsen, V. E. J. Chem. Educ. 2000, 77, 173. (b) Raviolo, A. J. Chem. Educ. 2001, 78, 629.
8. Singh, A. K.; Weaver, R. E.; Powers, G. L.; Rosso, V. R. U.S. Patent 6,-184,395, 2001.