159262-93-8

Usage

Derivation

Synthetic chemical compound derived from the natural product 10-deacetylbaccatin III, which is isolated from the yew tree.

Pharmaceutical Applications

Potential use as a precursor for the semisynthesis of paclitaxel, a widely used chemotherapy medication.

Stability and Solubility

The addition of the oxazolidine-5-carboxylate group enhances the stability and solubility of the baccatin III molecule.

Intermediate in Production

Valuable intermediate in the production of paclitaxel due to its enhanced stability and solubility.

Protective Group

The tert-butoxycarbonyl group in the molecule can protect certain functional groups during chemical reactions.

Efficient Synthetic Pathways

The protective group allows for more efficient and selective synthetic pathways in the production of paclitaxel.

Pharmaceutical Development

Significant potential for pharmaceutical development.

Contribution to Cancer Treatment

Can contribute to the production of essential cancer-fighting medications.

Chemical Structure

The compound has a complex structure with a phenyl group, a tert-butoxycarbonyl group, and an oxazolidine-5-carboxylate group attached to the baccatin III molecule.

Stereochemistry

The compound has specific stereochemistry, with the 4S,5R configuration at the oxazolidine ring.

Upstream product

• 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 
• 1122456-67-0 C₅₄H₆₇NO₁₄Si 
• 32981-86-5 10-deacetylbaccatin III 
• 143527-76-8 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 

Downstream Products

• 133524-69-3 (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-amino-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 
• 114915-20-7 Docetaxel 
• 162552-56-9 C₄₆H₅₆INO₁₃ 
• 159262-91-6 C₄₆H₅₅NO₁₃ 
• 158811-30-4 10-O-deacetyl larotaxel 
• 159262-90-5 C₃₈H₄₃NO₁₁ 
• 159262-92-7 C₄₇H₅₆F₃NO₁₆S 

Relevant academic research and scientific papers

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.

DOCETAXEL PROCESS AND POLYMORPHS

Processes for preparing substantially pure docetaxel, new crystalline forms of docetaxel and processes for preparation thereof, processes for preparing docetaxel trihydrate, and pharmaceutical compositions comprising docetaxel.

PROCESS FOR CONVERTING 9-DIHYDRO-13-ACETYLBACCATIN III INTO DOCETAXEL OR PACLITAXEL

Processes for the preparation of docetaxel and paclitaxel or analogs from 9-dihydro-13-acetylbaccatin III via key intermediates (4), (5), (6), (6'), (8) and (8') or via intermediate (12) as well as processes for the preparation of said intermediates are d

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.

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 access to 19-nor-7β, 8β-methylene-taxoids and formation of a 7-membered C-ring analog of doxetaxel by electrochemistry

A new route to semisynthetic 19-nor-7β, 8β-methylene taxoids, such as compound 8, from the 7-O-trifluoromethanesulfonyl derivative 6 is reported. Evidence for a dissociation of the triflate to form a carbocation at C-7 under the reaction conditions is pre