151509-27-2

Basic information

• Product Name: 2'-Ac-Docetaxel
• Synonyms: 2'-Ac-Docetaxel;2'-O-Acetyldocetaxel
• CAS NO: 151509-27-2
• Molecular Formula: C₄₅H₅₅NO₁₅
• Molecular Weight: 849.9159
• Mol File: 151509-27-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 901.3±65.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3 (20 ºC 760 Torr)
• PKA: 11.02±0.46(Predicted)
• CAS DataBase Reference: 2'-Ac-Docetaxel(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-Ac-Docetaxel(151509-27-2)
• EPA Substance Registry System: 2'-Ac-Docetaxel(151509-27-2)

Safety Data

• Hazardous Substances Data: 151509-27-2(Hazardous Substances Data)

Usage

General Description

2'-Ac-Docetaxel is a chemical compound that is derived from docetaxel, a chemotherapy medication used to treat various types of cancers. This modified form of docetaxel contains an acetyl group at the 2' position, which alters its chemical properties and potentially its efficacy. 2'-Ac-Docetaxel is designed to have improved solubility and stability, as well as potentially reduced toxicity compared to the original docetaxel. It is being studied for its potential use in cancer treatment, with the hope that it may offer improved therapeutic effects and reduce the side effects associated with traditional docetaxel treatment.

Upstream product

• 108-24-7 acetic anhydride 
• 114915-20-7 Docetaxel 
• 1056998-48-1 C₅₅H₇₁NO₁₉ 
• 1227402-72-3 N'-Boc-2'-acetyldocetaxel 
• 24424-99-5 di-tert-butyl dicarbonate 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 145514-62-1 RPR 130523 
• 1219592-76-3 (2R,3S)-N-Boc-3-phenylisoserine benzyl ester 
• 1219592-92-3 (2R,3S)-N-Boc-2-acetyl-3-phenylisoserine benzyl ester 
• 1219592-93-4 (2R,3S)-N,N-di-Boc-2-acetyl-3-phenylisoserine benzyl ester 
• 1219592-94-5 (2R,3S)-N,N-di-Boc-2-acetyl-3-phenylisoserine 
• 1227402-71-2 7,10-di-troc-N'-Boc-2'-acetyldocetaxel 

Downstream Products

• 114915-20-7 Docetaxel 

Relevant articles and documents

Conformation of Taxotere and analogues determined by NMR spectroscopy and molecular modeling studies

Taxol 1 and Taxotere 2 are antitumor compounds interacting with tubulin proteins. In order to find the best conformational fit to the receptor site, the structures of taxotere and twelve analogues showing various in vitro biological activity on tubulin, have been investigated by 1H NMR spectroscopy and molecular modeling studies. These structures were compared to that of Taxotere 2 obtained by X-ray analysis. The results obtained from these studies suggest that the most active 2′R,3′S compounds possess a conformation in which the benzoate group at C-2 holds the side chain in a defined position due to hydrophobic interactions between this group and the N-amido or N-carbonyloxy group at C-3′. This situation together with the presence of hydrogen bonding between 2′OH-3′NH and 2′OH-1′C - O gives rise to a specific orientation of the hydroxyl and phenyl groups at C-2′ and C-3′. On the other hand, the 2′S,3′R isomers which display low in vitro biological activity (ie: on tubulin), such as isotaxotere 8, possess a different conformation with no hydrophobic interactions between the side chain and the taxan skeleton.

METHOD FOR PREPARING TAXANE DERIVATIVES

Provided is a method for preparing a taxane derivative, comprising: carrying out condensation of a phenylisoserine derivatives having a protective group introduced thereto or a mixture of isomers thereof, as a side chain, with a baccatin III derivative or 10-deacetyl-baccatin III derivative to obtain a mixture of isomers; separating the isomers via chromatography; and carrying out a reversion of the stereochemical structure of a selectively separated isomer, which is suitable for producing a taxane derivative in a large scale with high yield.

METHOD FOR PREPARING TAXANE DERIVATIVES

Provided is a method for preparing a taxane derivative, comprising: carrying out condensation of a phenylisoserine derivatives having a protective group introduced thereto or a mixture of isomers thereof, as a side chain, with a baccatin III derivative or 10-deacetyl-baccatin III derivative to obtain a mixture of isomers; separating the isomers via chromatography; and carrying out a selective reversion of the stereochemical structure of a separated isomer, which is suitable for producing a taxane derivative in a large scale with high yield.