148930-55-6Relevant articles and documents
A CATALYTIC ASYMMETRIC METHOD FOR THE PREPARATION OF THE PACLITAXEL (TAXOL) C-13 SIDE-CHAIN DERIVATIVES AND ITS USE IN THE PREPARATION OF TAXANE DERIVATIVES
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Page/Page column 20-21, (2010/06/17)
A new catalytic asymmetric two-step or one-pot method for the preparation of the C-13 side-chain of paclitaxel (Taxol) and derivatives of the general formula (I) in the form of an acid, salt or ester, in which R represents an aryl group or alkyl group, R1 represents an aryl group or alkyl group, Y represents O, H or alkyl, and X1 represent -CH2-Ph, alkyl, aryl, SiR3 (where the silyl group is a common protective group) or other suitable protective group.
Trifluoroacetic acid-mediated cleavage of a triethylsilyl protecting group: Application in the final step of the semisynthetic route to paclitaxel (Taxol)
Singh, Ambarish K.,Weaver, Raymond E.,Powers, Gerald L.,Rosso, Victor W.,Wei, Chenkou,Lust, David A.,Kotnis, Atul S.,Comezoglu, F. Taha,Liu, Mark,Bembenek, Kenneth S.,Phan, Bich D.,Vanyo, Dale J.,Davies, Merrill L.,Mathew, Rachel,Palaniswamy, Venkatapuram A.,Li, Wen-Sen,Gadamsetti, Kumar,Spagnuolo, Ciro J.,Winter, William J.
, p. 25 - 27 (2013/09/05)
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.
Total asymmetric synthesis of taxol by dehydration condensation between 7-TES baccatin III and protected N-benzoylphenylisoserines prepared by enantioselective aldol reaction
Shiina, Isamu,Saitoh, Katsuyuki,Frechard-Ortuno, Isabelle,Mukaiyama, Teruaki
, p. 3 - 4 (2007/10/03)
Total asymmetric synthesis of Taxol was completed by dehydration condensation between a protected N-benzoylphenylisoserine 4 or 9 and 7-TES baccatin in which was prepared from 8-membered ring enone. Taxol side chains 4, 7, 9 and 11, optically active protected N-benzoylphenylisoserines, were successfully synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether derived from S-ethyl benzyloxyethanethioate.