Trifluoroacetic Acid-Mediated Cleavage of a Triethylsilyl Protecting Group:  Application in the Final Step of the Semisynthetic Route to Paclitaxel (Taxol)

Autor: Singh, A. K., Weaver, R. E., Powers, G. L., Rosso, V. W., Wei, C., Lust, D. A., Kotnis, A. S., Comezoglu, F. T., Liu, M., Bembenek, K. S., Phan, B. D., Vanyo, D. J., Davies, M. L., Mathew, R., Palaniswamy, V. A., Li, W.-S., Gadamsetti, K., Spagnuolo, C. J., Winter, W. J.
Zdroj: Organic Process Research & Development; January 2003, Vol. 7 Issue: 1 p25-27, 3p
Abstrakt: The final step of the semisynthetic route to paclitaxel involves cleavage of the triethylsilyl (TES) protecting group from the C-7 hydroxyl group. Paclitaxel is an extremely complex molecule, and standard deprotection conditions led to formation of several impurities. Trifluoroacetic acid in aqueous acetic acid was found to be very effective in the cleavage of the TES group without compromising the quality of the product.
Databáze: Supplemental Index