143527-76-8

Usage

Uses

Used in Pharmaceutical Industry:
13-[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl-10-deacetyl-7,10-bis[(2,2,2-trichloroethyl)oxy]carbonyl Baccatin III is used as an intermediate in the synthesis of Docetaxel metabolites for its antineoplastic properties. 13-[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl-10-deacetyl-7,10-bis[(2,2,2-trichloroethyl)oxy]carbonyl Baccatin III contributes to the development of cancer treatments by enhancing the effectiveness of chemotherapy and potentially improving patient outcomes.
Used in Anticancer Applications:
As an intermediate in the synthesis of Docetaxel metabolites, 13-[(3-N-Boc)-2,2-dimethyl-4S-phenyl-1,3-oxazolidin-5R-yl]formyl-10-deacetyl-7,10-bis[(2,2,2-trichloroethyl)oxy]carbonyl Baccatin III plays a significant role in the development of anticancer drugs. It aids in the creation of medications that target and inhibit the growth of cancer cells, offering a promising avenue for cancer treatment and management.
Used in Drug Delivery Systems:
The compound may also be utilized in the development of novel drug delivery systems, aiming to improve the bioavailability and therapeutic outcomes of Docetaxel and its metabolites. By employing various organic and metallic nanoparticles as carriers, the compound can enhance the delivery and efficacy of antineoplastic agents, potentially leading to better treatment options for cancer patients.

Upstream product

• 100-52-7 benzaldehyde 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 143527-74-6 ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 32981-86-5 10-deacetylbaccatin III 
• 143527-75-7 (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 95603-44-4 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 

Downstream Products

• 114915-16-1 10-deacetyl-7,10-diTroc-baccatin III 
• 114915-20-7 Docetaxel 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 114915-18-3 C₅₁H₅₁Cl₆NO₁₇ 
• 159262-92-7 C₄₇H₅₆F₃NO₁₆S 
• 162552-56-9 C₄₆H₅₆INO₁₃ 

Relevant academic research and scientific papers

Method for purifying docetaxel

The invention discloses a method for purifying docetaxel. A docetaxel solid precipitates from a dichloromethane and toluene mixed solution. The purifying method has the advantages of great reduction of the single content of every impurity in docetaxel, introduction of few impurities, improvement of the purity of the product, and high yield, and is very suitable for industrial large-scale production, and the obtained product meets preparation demands, and can be directly used to prepare a docetaxel injection.

Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs

By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, α,α-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol.

Alternative synthesis and the determination of absolute configuration of docetaxel, an anticancer drug

A simple, efficient, and alternative synthetic route for docetaxel with better control on the protection-deprotection sequence has been developed. The process is easily scalable and commercially viable, and critical impurities can be controlled efficiently. For the first time, absolute configuration of docetaxel was determined unambiguously by single-crystal X-ray diffraction.

PREPARATION OF DOCETAXEL

The present invention relates to docetaxel and processes for preparing docetaxel, including process-related intermediates. The present invention also relates to processes for preparing substantially pure docetaxel and intermediates.

Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues

A series of novel fluorinated docetaxel analogues have been synthesized and evaluated in vitro and in vivo. Incorporated one, two or three fluorine atom(s) either at both meta position on C-2 benzolate and 3′-N-tert-butyloxyl group or only at 3′-N-tert-butyloxyl group has resulted in potent analogues which have comparable or superior in vitro and in vivo cytotoxicity to docetaxel. Among them, compounds 14d and 14e have displayed more potent cytotoxicity than docetaxel both in human cancer cell line SK-OV-3 in vitro and in human non-small cell lung cancer A549 xenografts in vivo. Preliminary data show that compound 14a has reduced acute animal toxicity in mice compared with docetaxel.

DOCETAXEL POLYMORPHS AND PROCESSES

The present invention provides crystalline polymorphs of docetaxel and processes for preparing them, a method for preparing amorphous docetaxel, and a process for preparing docetaxel.

Taxotere by esterification with stereochemically 'wrong' (2S,3S)- phenylisoserine derivatives

Cyclically protected anti (2S,3S) phenylisoserines on esterification with baccatin III derivatives afford Taxotere and taxol precursors with the syn (2'R, 3'S) side chain.

Preparation of 7-Modified docetaxel analogs using electrochemistry

The electrochemical reduction of 7α -iodo docetaxel at E- 1.3V vs. SCE in methanol in the presence of lithium chloride and hydrochloric acid leads predominantiy to 7-deoxy-ocetaxel 9. When the electroreduction is conducted at E-1.7V vs. SCE in the presenc

Improved protection and esterification of a precursor of the taxotere and taxol side chains

(4S,5R)-N-BOC-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a,b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere, taxol and analogs.