115437-18-8

Usage

Uses

Used in Organic Synthesis:
7-O-(Triethylsilyl)-10-deacetyl Baccatin III is used as a synthetic intermediate for the preparation of various complex organic molecules. Its unique structural features make it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 7-O-(Triethylsilyl)-10-deacetyl Baccatin III is used as a key intermediate in the synthesis of paclitaxel, a widely used anticancer drug. Its unique functional groups facilitate the formation of the desired paclitaxel structure, making it an essential component in the development of this life-saving medication.
Used in Agrochemical Industry:
7-O-(Triethylsilyl)-10-deacetyl Baccatin III is also utilized in the agrochemical industry as a precursor for the synthesis of various bioactive compounds. Its versatility in organic synthesis allows for the creation of new agrochemicals with improved efficacy and selectivity, contributing to more sustainable agricultural practices.
Used in Specialty Chemicals:
7-O-(Triethylsilyl)-10-deacetyl Baccatin III is employed in the synthesis of specialty chemicals, such as fragrances, dyes, and other high-value compounds. Its unique properties enable the development of novel products with specific applications in various industries, including cosmetics, textiles, and coatings.

InChI:InChI=1/C35H50O10Si/c1-9-46(10-2,11-3)45-24-17-25-34(19-42-25,44-21(5)36)28-30(43-31(40)22-15-13-12-14-16-22)35(41)18-23(37)20(4)26(32(35,6)7)27(38)29(39)33(24,28)8/h12-16,23-25,27-28,30,37-38,41H,9-11,17-19H2,1-8H3/t23-,24-,25+,27+,28?,30-,33+,34-,35+/m0/s1

Upstream product

• 155588-21-9 7-triethylsilyl-13-dehydro-10-deacetylbaccatin III 
• 32981-86-5 10-deacetylbaccatin III 
• 994-30-9 triethylsilyl chloride 
• 152448-78-7 13-Acetyl-7-(triethylsilyl)baccatin III 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 183743-19-3 7-TES-9,10-diketobaccatin III 

Downstream Products

• 149140-53-4 C₄₂H₄₉F₅O₁₁SSi 
• 144654-43-3 4,10-bis(deacetyl)-7-(triethylsily)baccatin III 
• 181705-99-7 7-triethylsilyl-10-(4-morpholine-N-carbonyl)-10-deacetylbaccatin III 
• 181961-55-7 7-triethylsilyl-10-(E-but-2-enoyl)-10-deacetylbaccatin III 
• 181705-96-4 C₄₁H₆₀O₁₁Si 
• 178250-12-9 7-triethylsilyl-10-propanoyl-10-deacetylbaccatin III 
• 181706-05-8 C₄₂H₆₁NO₁₁Si 
• 181706-00-3 C₃₇H₅₃NO₁₁Si 
• 152448-78-7 13-Acetyl-7-(triethylsilyl)baccatin III 
• 618428-08-3 7-triethylsilyl-10-tetradecanoyl-10-deacetylbaccatin III 
• 618428-09-4 7-triethylsilyl-10-phenylacetyl-10-deacetylbaccatin III 
• 872852-70-5 C₄₂H₄₄O₁₁ 
• 178250-27-6 SB-T-1102 
• 178250-30-1 3'-dephenyl-10-(methoxycarbonyl)-3'-(2-methylpropyl)-docetaxel 

Relevant academic research and scientific papers

Synthesis of modified baccatins via an oxidation-reduction protocol

(12R)-7-trietylsilyl-11-dihydro-10-deacetylbaccatin III (2), -deacetylbaccatin III (4) and the 7,8-seco baccatin III (5a) were synthesized from 10-deacetylbaccatin III via an oxidation-reduction protocol.

New and effective synthesis of 7-triethylsilylbaccatin III from 7β,13α-bistriethylsiloxy-1β,2α,10β-trihydroxy-9-oxo- 4(20),11-taxadiene

7β,13α-Bistriethylsiloxy-1β,2α,10β-trihydroxy -9- oxo-4(20), 11-taxadiene (2), derived from 10-deacetylbaccatin III via degradation of oxetane ring, was conveniently converted into 7-triethylsilylbaccatin III (1) by way of a new and effective method for constructing oxetane ring. Thus, the synthesis of a precursor of taxol from novel taxoid 2 was accomplished.

A facile one-pot synthesis of 7-triethylsilylbaccatin III

A one-pot synthesis of 7-triethylsilylbaccatin III has been delineated. The reaction can easily be extended for the preparation of analogs of baccatin III.

Antagonizing NOD2 Signaling with Conjugates of Paclitaxel and Muramyl Dipeptide Derivatives Sensitizes Paclitaxel Therapy and Significantly Prevents Tumor Metastasis

A noncleavable paclitaxel (PTX) and N-acetylmuramyl-l-alanyl-d-isoglutamine (MDP) derivative conjugate, 22 (DY-16-43), and its analogues were prepared and characterized as antagonists of NOD2 signaling. This conjugate enhanced the antitumor and antimetastatic efficacy of PTX in Lewis lung carcinoma (LLC) tumor-bearing mice. This work first describes a molecular strategy that enables the sensitization of a chemotherapeutic response via antagonizing NOD2 inflammatory signaling and suggests NOD2 antagonist as potential adjunct in treating non-small-cell lung cancer (NSCLC).

Total synthesis of Taxol. 1. Retrosynthesis, degradation, and reconstitution

A successful strategy for the enantioselective synthesis of the natural stereoisomer of Taxol (1) has been developed. This strategy utilized the convergent assembly of Taxol's central eight-membered B ring from preformed synthons for rings A (10) and C (9) followed by late introduction of the D ring and side chain. Degradative studies confirmed the viability of certain crucial manipulations including oxidation of the C13 position (35 → 3) and regioselective introduction of the C1-hydroxyl, C2-benzoyloxy moiety (29 → 31). Additionally, a convenient method for the large-scale production of 29, a derivative useful for C2 analog production, was developed.

β-Selective Aroylation of Activated Alkenes by Photoredox Catalysis

Late-stage synthesis of α,β-unsaturated aryl ketones remains an unmet challenge in organic synthesis. Reported herein is a photocatalytic non-chain-radical aroyl chlorination of alkenes by a 1,3-chlorine atom shift to form β-chloroketones as masked enones

Fluorinated taxane compound, preparation method therefor and application of fluorinated taxane compound

The invention discloses a fluorinated taxane compound, a preparation method therefor and an application of the fluorinated taxane compound. The compound has a structural general formula represented bya formula I. Proven by pharmacological experiments, compared with paclitaxel, a series of fluorinated taxane derivatives synthesized by the method have cytotoxicity superior to that of the paclitaxelto a multidrug-resistant human mammary cancer cell line MCF-7/Adr and an ovarian cancer cell line NCI/Adr and represent cytotoxicity superior to that of the paclitaxel to a colon cancer cell line HCT-116 with overexpressed neoplasm stem cells.

Preparation method of taxane compound and intermediate of taxane compound

The invention provides a preparation method of a taxane compound and an intermediate of the taxane compound. The preparation method of a TPI-287 intermediate A starts with a starting step of a raw material 10-deacetylbaccatin III (also named as 10-DAB), a

Preparation method of 10,13-two-branched-chain-taxol

The invention discloses a preparation method of 10,13-two-branched-chain-taxol. The preparation method comprises the following steps: taking 10-Dab as a raw material; protecting 7-hydroxyl by using a silyl ether protecting agent; simultaneously condensing

Methods for preparing semi-synthetic paclitaxel and intermediate thereof

The invention relates to methods for preparing semi-synthetic paclitaxel and an intermediate thereof. The method for preparing the semi-synthetic paclitaxel comprises the following steps: dissolving 10-DABIII (10-deacetylbaccatinIII) into pyridine, protecting hydroxyl on position-7 carbon on the 10-DABIII with triethyl silicyl to obtain an intermediate I, acetylating hydroxyl on position-10 carbon of the intermediate I to obtain an intermediate II, reacting the intermediate II, a side-chain radical compound and 4-dimethylaminopyridine in an organic solvent to prepare an intermediate III, and reacting the intermediate III with trifluoroacetic acid under an acidic condition to obtain a crude paclitaxel product. The preparation methods are simple and easy for industrialization; the active hydroxyl of the raw material 10-DABIII is effectively protected, so that fewer byproducts are finally generated, and a prepared paclitaxel product has high molar yield of 70 to 81 percent and high paclitaxel purity of 99.5 to 99.9 percent; the residual rate of the raw material in the steps of synthesizing the intermediate II and synthesizing the paclitaxel is low, side reactions are reduced, and the raw material is high in reaction selectivity and utilization rate; the product can be directly used as a raw material for the medical field of treatment of ovarian cancer, breast cancer and the like.