148930-55-6

Basic information

• Product Name: 7-O-(Triethylsilyl) Paclitaxel
• Synonyms: 7-O-(Triethylsilyl) Paclitaxel;(αR,βS)-β-(BenzoylaMino)-α-hydroxy-benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-Bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetraMethyl-5-oxo-4-[(triethylsilyl)oxy]-7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl Ester;7-O-(Triethylsilyl)taxol;Paclitaxel EP Impurity K
• CAS NO: 148930-55-6
• Molecular Formula: C₅₃H₆₅NO₁₄Si
• Molecular Weight: 968.167
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 148930-55-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: 7-O-(Triethylsilyl) Paclitaxel(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-(Triethylsilyl) Paclitaxel(148930-55-6)
• EPA Substance Registry System: 7-O-(Triethylsilyl) Paclitaxel(148930-55-6)

Safety Data

• Hazardous Substances Data: 148930-55-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7-O-(Triethylsilyl) Paclitaxel is used as a protected form of Paclitaxel for the purpose of enhancing its stability and solubility. This modification allows for better protection of the drug during synthesis and formulation processes, ultimately leading to improved efficacy and reduced impurities, such as Impurity K.
Used in Anticancer Applications:
As a derivative of Paclitaxel, 7-O-(Triethylsilyl) Paclitaxel is employed as an anticancer agent, targeting various types of cancer cells. Its improved chemical properties and enhanced stability make it a valuable asset in the development of novel cancer treatments, potentially offering better therapeutic outcomes and reduced side effects compared to traditional Paclitaxel formulations.
Used in Drug Delivery Systems:
7-O-(Triethylsilyl) Paclitaxel can be utilized in the development of advanced drug delivery systems, such as nanoparticles or liposomes, to improve the bioavailability and targeted delivery of Paclitaxel. These systems can enhance the drug's therapeutic effects while minimizing potential side effects, making it a valuable component in the design of innovative cancer treatments.

Upstream product

• 994-30-9 triethylsilyl chloride 
• 35804-44-5 ethyl 4-bromo-4-pentenoate 
• 175982-36-2 (4S,4aS,6R,9S,11S,12S,12aR)-11,12-(Carbonyldioxy)-4a,8,13,13-tetramethyl-1-methylene-5-oxo-4,9-bis(triethylsiloxy)-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-38-4 (2S,4S,4aS,6R,9S,11S,12S,12aS)-2-Bromo-11,12-(carbonyldioxy)-4a,8,13,13-tetramethyl-1-methylene-5-oxo-4,9-bis(triethylsiloxy)-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-37-3 (4S,4aS,6R,9S,11S,12S,12aS)-1-Bromomethyl-11,12-(carbonyldioxy)-4a,8,13,13-tetramethyl-5-oxo-4,9-bis(triethylsiloxy)-3,4,4a,5,6,9,10,11,12,12a-decahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-40-8 1,2-O,O-Carbonyl-7,13-O,O-bis(triethylsilyl)-4-deacetyl-2-debenzoylbaccatin III 
• 175982-39-5 (1S,2S,4S,4aS,6R,9S,11S,12S,12aR)-2-Bromo-11,12-(carbonyldioxy)-1-hydroxy-1-hydroxymethyl-4a,8,13,13-tetramethyl-5-oxo-4,9-bis(triethylsiloxy)-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 175982-31-7 1,2-O,O-Carbonyl-7,13-O,O-bis(triethylsilyl)-2-debenzoylbaccatin III 
• 178626-24-9 2-bromo-5-(triethylsilyloxy)pentene 
• 202340-92-9 (1S,4aR,5S,6S,9R,10R,11S,12S,12aS)-1,12-(Isopropylidenedioxy)-9,12a,13,13-tetramethyl-4-methylenetetradecahydro-6,10-methanobenzocyclodecene-5,6,9,10,11-pentaol 
• 222727-00-6 (4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-11,12-(Carbonyldioxy)-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecene-5,7,8-triol 
• 202340-94-1 (4S,4aS,5S,6S,7R,8R,11S,12S,12aR)-11,12-(Carbonyldioxy)-7,8-dihydroxy-4,5-(isopropylidenedioxy)-4a,8,13,13-tetramethyl-1-methylenetetradecahydro-7,11-methanobenzocyclodecen-6-yl acetate 
• 202340-82-7 (1R,2S,3S,5R,6R,7S,8S,9S)-2,6-Dibenzyloxy-3-(3-butenyl)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3,5-diol 
• 194420-27-4 (4S,4aS,6R,11S,12S,12aR)-11,12-(Carbonyldioxy)-4a,8,13,13-tetramethyl-1-methylene-5-oxo-4-triethylsiloxy-1,2,3,4,4a,5,6,9,10,11,12,12a-dodecahydro-7,11-methanobenzocyclodecen-6-yl acetate 

Downstream Products

• 160237-31-0 C₅₅H₆₉NO₁₄SSi 
• 148930-30-7 2’-carboxybenzoylpaclitaxel 
• 160237-32-1 C₄₉H₅₅NO₁₄S 
• 160237-25-2 BMS-184476 
• 160237-27-4 C₅₇H₆₁NO₁₆S 
• 160237-33-2 C₆₂H₆₆NO₁₈P 
• 33069-62-4 taxol 
• 115437-21-3 7-(triethylsilyl)baccatin III 

Relevant 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

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.

Highly enantioselective organocatalytic addition of aldehydes to N-(Phenylmethylene)benzamides: Asymmetric synthesis of the paclitaxel side chain and its analogues

A simple highly enantioselective organocatalytic addition of aldehydes to N-(phenylmethylene)benzamides is presented. The application of (R)-proline as the catalyst and subsequent oxidation of the protected α-hydroxy-β- benzoylami-noaldehydes (92-99% ee) gives access to esterification-ready phenylisoserine derivatives such as the protected paclitaxel (taxol) side chain. Esterification of these derivatives with baccatin III gives access to the cancer chemotherapeutic substance paclitaxel and its analogues that do not exist in nature.

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

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.

Asymmetric total synthesis of Taxol

The asymmetric total synthesis of Taxol was achieved by way of B to BC to ABC to ABCD ring construction. Optically active 8-membered ring enones 1 and 2 corresponding to the B ring of Taxol have been synthesized in high yields from the linear precursors 28 and 32, respectively, by intramolecular aldol cyclization using SmI2. The optically active linear polyoxy compounds 28 and 32 were obtained by way of diastereoselective aldol reaction between aldehyde 4 and ketene silyl acetal 8 catalyzed by MgBr2 · OEt2. The chiral pentanal 4 was synthesized either by asymmetric aldol reaction of achiral aldehyde 7 and ketene silyl acetal 8 by means of a chiral Lewis acid or by diastereoselective aldol reaction between the chiral aldehyde 16, derived from L-serine, and the lithium enolate derived from methyl isobutyrate. Optically active bicyclo[6.4.0]dodecanone 38β, corresponding to the BC ring system of Taxol, was prepared from 8-membered ring enone 2 in high yield by stereoselective Michael addition and successive intramolecular aldol cyclization. Furthermore, baccatin III, the ABCD ring system of Taxol, was efficiently synthesized from the BC ring system 38β by successive construction of the A and D rings by intramolecular pinacol coupling cyclization, introduction of the C-13 hydroxyl group and an oxetane-forming reaction. Finally, the total synthesis of Taxol was accomplished by dehydration condensation between a protected N-benzoylphenylisoserine 70 or 75 and 7-TES baccatin III, prepared from baccatin III. Taxol side chains 70, 73, 75, and 77, optically active protected N-benzoylphenylisoserines, were synthesized by enantioselective aldol reaction from two achiral starting materials, benzaldehyde and an enol silyl ether 65 derived from S-ethyl benzyloxyethanethioate.

Total asymmetric synthesis of taxol by dehydration condensation between 7-TES baccatin III and protected N-benzoylphenylisoserines prepared by enantioselective aldol reaction

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.

Synthesis and antitumor evaluation of paclitaxel phosphonooxymethyl ethers: A novel class of water soluble paclitaxel pro-drugs

The synthesis, pharmacokinetic properties, and antitumor evaluation of novel paclitaxel phosphonooxymethyl ether derivatives 8-11 and salts thereof is described. These compounds exhibit improved water solubility as compared to paclitaxel (1) and upon incubation with plasma and alkaline phosphatase they readily release parent drug. The in vivo antitumor evaluation of compounds 8-11 established them as suitable pro-drugs of paclitaxel.

THE CHEMISTRY OF TAXANES: REACTIONS OF TAXOL AND BACCATIN DERIVATIVES WITH LEWIS ACIDS IN APROTIC AND PROTIC MEDIA

Several Lewis acids were shown to cleanyl open the oxetane ring of taxol and baccatin derivatives.The reaction is shown to proceed via anchimeric assistance by the C-4 acetate group.Several minor products, including a novel derivative possessing a bridged C-ring, were also isolated.A mechanistric rationale is provides for all compounds formed.When taxol derivatives were treated with Lewis acids in methanol, ester cleavage reactions were observed.We provide conditions that are selective for C-10 acetate cleavage and for C-13 side-chain methanolysis.