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
• Article Data: 8

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

Description

7-O-(Triethylsilyl) Paclitaxel is a chemical derivative of the naturally occurring compound Paclitaxel, which is a widely used chemotherapeutic agent. This derivative is characterized by the presence of a triethylsilyl group at the 7-O position, which provides enhanced stability and solubility compared to the parent compound. As a pale beige solid, it exhibits improved chemical properties that make it a promising candidate for various pharmaceutical applications.

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

• 33069-62-4 taxol 
• 994-30-9 triethylsilyl chloride 
• 148930-30-7 2’-carboxybenzoylpaclitaxel 
• 202390-83-8 5-Ethyl (2R,3S)-3-benzoylamino-2-benzyloxy-3-phenylpropanethioate 
• 194420-31-0 (2R,3S)-2-benzyloxy-3-benzoylamino-3-phenylpropanoic acid 
• 202390-82-7 5-Ethyl (2R,3S)-3-amino-2-benzyloxy-3-phenylpropanethioate 
• 129320-33-8 5-Ethyl (2R,3R)-2-benzyloxy-3-hydroxy-3-phenylpropanethioate 
• 194420-15-0 (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-{1-[3-(triethylsiloxy)propyl]vinyl}cyclooctanone 
• 222726-93-4 (2R,3R,5R,6S,7S,8S)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-[1-(3-hydroxypropyl)vinyl]-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone 
• 194420-16-1 4-[(1S,2S,3R,5R,6R,8S)-2,6-Dibenzyloxy-5-(tert-butyldimethylsiloxy)-3-(p-methoxybenzyloxy)-4,4,8-trimethyl-7-oxocyclooctyl]-4-pentenal 
• 194420-21-8 (1R,2S,3S,5R,6S,7S,8S,9S)-2,6-Dibenzyloxy-3-(3-butenyl)-5-(tert-butyldimethylsiloxy)-7,9-(isopropylidenedioxy)-4,4,8-trimethyl-12-methylenebicyclo[6.4.0]dodecan-3-ol 
• 222727-03-9 (4S,4aS,6R,9S,11S,12S,12aR)-11,12-(Carbonyldioxy)-9-hydroxy-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 
• 194420-23-0 (1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(dicyclohexylmethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylene-6-(3-oxobutyl)bicyclo[6.4.0]dodecan-4-one 
• 222726-98-9 (1S,2S,3S,6S,7S,8R,12S)-3,7-Dibenzyloxy-6-(3-butenyl)-6-(dicyclohexylmethylsiloxy)-2,12-(isopropylidenedioxy)-1,5,5-trimethyl-9-methylenebicyclo[6.4.0]dodecan-4-one 

Downstream Products

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

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.

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.

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.