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Usage

Uses

Used in Pharmaceutical Industry:
7-(triMethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydro oxazol-5-yl)carbonyl]baccatin III is used as a precursor in the semi-synthesis of paclitaxel, a widely used chemotherapy medication. Its unique chemical modifications may improve the compound's properties for drug development, enhancing the efficacy and safety of paclitaxel-based treatments.
Used in Drug Development:
7-(triMethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydro oxazol-5-yl)carbonyl]baccatin III is used as a chemical intermediate for the development of novel therapeutic agents. The triMethylsilyl and oxazol-5-yl carbonyl groups may provide specific advantages, such as increased stability, solubility, or bioavailability, making it a promising candidate for the creation of new drugs with improved pharmacological profiles.
Used in Chemical Industry:
7-(triMethylsilyl)-13-O-[((4S,5R)-2,4-diphenyl-4,5-dihydro oxazol-5-yl)carbonyl]baccatin III is used as a building block in the synthesis of complex organic compounds. Its unique structure and functional groups can be utilized in various chemical reactions, enabling the production of new molecules with diverse applications in materials science, agrochemicals, and other fields.

Upstream product

• 146848-91-1 (4S,5R)-2,4-diphenyl-2-oxazoline-5-carboxylic acid methyl ester 
• 718627-85-1 C₂₁H₁₈N₄O₅ 
• 115437-21-3 7-(triethylsilyl)baccatin III 
• 718627-86-2 C₃₁H₂₂N₄O₅ 
• 181294-27-9 (2S,3S)-3-Benzoylamino-2-hydroxy-3-phenyl-thiopropionic acid S-phenyl ester 
• 235432-34-5 3-N-benzoyl-4-phenyl-(4S,5R)-2-oxo-1,2,3-oxathiazolidine methyl ester 
• 235432-33-4 3-N-benzoyl-4-phenyl-(4S,5R)-2-oxo-1,2,3-oxathiazolidine methyl ester 
• 235432-35-6 3-N-benzoyl-4-phenyl-(4S,5R)-2,2-dioxo-1,2,3-oxathiazolidine methyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 260249-48-7 C₆₁H₇₁NO₁₆Si 
• 260249-49-8 C₅₉H₆₉NO₁₅Si 
• 260249-52-3 C₅₉H₆₉NO₁₅Si 
• 260249-47-6 C₅₉H₆₇N₃O₁₄Si 
• 260249-46-5 C₅₉H₆₉NO₁₄Si 

Downstream Products

• 623149-02-0 2'-deoxy-2'-epi-acetylmercapto-7-O-(triethylsilyl)paclitaxel 
• 153652-62-1 C₄₇H₄₉NO₁₃ 
• 158800-38-5 C₄₇H₄₉NO₁₃ 
• 623149-03-1 2'-deoxy-2'-epi-acetylmercaptopaclitaxel 
• 33069-62-4 taxol 

Relevant academic research and scientific papers

THE METHOD FOR PRODUCTION OF SEMI-FINISHED PRODUCTS USEFUL IN SYNTHESIS OF PACLITAXEL

The method for production of the semi-finished products useful in synthesis of Paclitaxel with the generalized formula (2), characterized in that phenyl isoserine derivatives, or mixtures of their epimerides with various configurations on the carbon 2' or their salts, are treated with triazine type condensing agent, possible in the presence of tertiary amine, in medium of anhydrous organic solvent, and the triazine esters produced are treated with Baccatin III, in medium of anhydrous organic solvent, possible in the presence of a catalyst.

Synthesis of novel thiol surrogate of Taxol: 2′-deoxy-2′- mercaptopaclitaxel

Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of the exact thiol surrogate product of

Synthesis of novel taxoid analogue containing sulfur group on C-13 side-chain: 2′-deoxy-2′-epi-mercaptopaclitaxel

Paclitaxel analogues with a thiol group in place of the hydroxyl group on the C-13 side-chain constitute an interesting avenue of research for the study of new taxoid compounds. A synthetic route for the preparation of 2′-deoxy-2′-epi-mercaptopaclitaxel w

A semisynthesis of paclitaxel via a 10-deacetylbaccatin III derivative bearing a β-keto ester appendage

A semisynthesis of paclitaxel has successfully been accomplished starting from a newly developed baccatin III derivative bearing a β-keto ester appendage on C-13.

A new semisynthesis of paclitaxel from Baccatin III

A new method for the semisynthesis of paclitaxel (Taxol) from baccatin III via a dioxo-oxathiazolidine intermediate is reported.

Taxol semisynthesis: A highly enantio- and diastereoselective synthesis of the side chain and a new method for ester formation at C-13 using thioesters

A very simple, new, and straightforward approach to the Paclitaxel (Taxol) and Docetaxel (Taxotere) side chains has been developed using the imine addition reaction of thioester-derived boron enolates bearing chiral ligands. The addition reaction was studied extensively, using a combination of different thioesters (ROCH2COSPh, ROCH2COSt-Bu), oxygen protecting groups (R = Bn, TBDMS, COPh, EE, TMS), chiral boron ligands [derived from both (-) and (+)-menthone], imines (PhCH=NSiMe3, PhCH=NCOPh), and in the presence or in the absence of additional Lewis acids (BF3-OEt2, Et2AlCl, TiCl4). The side chain was assembled in a few steps with the correct relative (syn) and absolute stereochemistry (2R,3S). The stereochemical outcome of the boron-mediated reaction was rationalized using chair vs boat transition state structures. A new direct route for attachment of the side chains to the baccatin nucleus using thioester chemistry has also been developed. By treatment of a mixture of a thioester (8, 12, or 17) and protected baccatin III (2b, 2c) with LHMDS, the 13-0 acylated compounds were obtained in high yield (up to 90%). Hydrolysis of 18b gave Paclitaxel (1a) in 80% yield.

Synthesis of Taxol from Baccatin III via an Oxazoline Intermediate

Taxol (1) can be prepared in good yield by coupling the oxazoline carboxylic acid 5 with 7-(triethylsilyl)baccatin III, followed by hydrolysis.The oxazolines 7 and 8 can also be prepared directly from taxol.