183133-99-5

Basic information

• Product Name: 7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III
• Synonyms: 7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III
• CAS NO: 183133-99-5
• Molecular Formula: C₄₁H₆₄O₁₀Si₂
• Molecular Weight: 773.11186
• Product Categories: Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 183133-99-5.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III(CAS DataBase Reference)
• NIST Chemistry Reference: 7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III(183133-99-5)
• EPA Substance Registry System: 7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III(183133-99-5)

Safety Data

• Hazardous Substances Data: 183133-99-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III is used as a key intermediate for the preparation of taxol analogs, which are known for their antitumoral and antineoplastic properties. The compound plays a crucial role in the development of cancer-fighting drugs due to its ability to inhibit tumor growth and progression.
Used in Cancer Research:
In the field of cancer research, 7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III is utilized as a starting material for the synthesis of taxol analogs. These analogs have the potential to target various types of cancer cells, making the compound an essential tool in the ongoing fight against cancer.
Used in Drug Development:
7,13-Bis-O-(triethylsilyl)-10-deacetyl Baccatin III is employed as a vital component in the development of novel drug delivery systems. Its use in the synthesis of taxol analogs allows for the creation of more effective and targeted cancer treatments, ultimately improving patient outcomes and survival rates.

Upstream product

• 32981-86-5 10-deacetylbaccatin III 
• 994-30-9 triethylsilyl chloride 

Downstream Products

• 183133-98-4 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-9-oxo-10β-methoxy-7β,13α-di(triethylsilyloxy)-11-taxene 
• 183133-94-0 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxene 
• 1433749-82-6 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,7β-dihydroxy-9-oxo-10β-methoxy-13α-triethylsilyloxy-11-taxene 
• 1396601-24-3 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β-hydroxy-7β,10β-dimethoxy-9-oxo-13-(triethylsilyloxy)-11-taxene 
• 183133-96-2 carbazitaxel 
• 1402820-62-5 (αR, βS)-α-hydroxy-β-[[(1,1-dimethylethoxy)carbonyl]amino]benzene-propanoic acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,1112,12a,12b-dodecahydro-11-hydroxy-4,6-dimethoxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester isopropanol solvate 
• 237428-99-8 C₇₁H₁₀₄O₂₀Si₂ 

Relevant articles and documents

Preparation method of 7beta,10beta-dimethoxy-10-deacetylbaccatin III

The invention relates to a preparation method of 7beta,10beta-dimethoxy-10-deacetylbaccatin III. Particularly, the method provided by the invention takes acetylbaccatin as a raw material and comprises a series of the following steps: protecting through silicon protecting groups at a 7 site and a 13 site; selectively removing the silicon protecting group at the 7 site; directly alkylating at the 7 site and a 10 site; and finally, removing the silicon protecting group at the 13 site to prepare a taxane compound, namely the 7beta,10beta-dimethoxy-10-deacetylbaccatin III shown as a formula V. (The formula V is shown in the description.).

PROCESS FOR THE PREPARATION CABAZITAXEL

The present invention discloses a process for the preparation of 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-7β,10β-dimethoxy-9-oxotax-11-en-13α-yl(2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenyl-propionate Cabazitaxel (I).

PROCESSES FOR THE PREPARATION OF CABAZITAXEL INVOLVING C(7) -OH AND C(13) -OH SILYLATION OR JUST C(7) -OH SILYLATION

Disclosed are processes towards Cabazitaxel (I) starting from 10-Deacetylbaccatin (III) that involve steps of either 7-OH monosilylation (passing through formula V) or 7,13-disilylation (passing through formulae XI, XII). Isopropanol Solvates of Cabazitaxel and processes to make this are also described.

Synthesis of paclitaxel (docetaxel) / 2-deacetoxytaxinine J dimers

Starting from taxanes available in multigram amounts from widespread ornamental yews (10-deacetylbaccatin III (4) and 2'-deacetoxyaustrospicatine (5)), two dimeric taxoids (3a, 3b) with potential dual target specificity (β-tubulin and P-gp) were synthesised. Both compounds lacked significant cytotoxicity, though 3b retained a strong activity in the tubulin depolimerisation assay.