95603-44-4

Basic information

• Product Name: 7,10-Bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III
• Synonyms: 7,10-Bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III;7,10-Bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III;7,10-Di(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III;7,10-Di-O-[(2,2,2-trichloroethoxy)carbonyl]baccatin III;7,10-DiTroc-10-deacetylbaccatin III;Carbonic Acid (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-9,11-dihydroxy-4a,8,13,13-tetraMethyl-5-oxo-7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete-4,6-diyl bis(2,2,2-trichloroethyl) Ester;7,10-Troc-10-DAB;0-Troc-10-DAB
• CAS NO: 95603-44-4
• Molecular Formula: C₃₅H₃₈Cl₆O₁₄
• Molecular Weight: 895.38582
• Product Categories: Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals
• Mol File: 95603-44-4.mol
• Article Data: 17

Chemical Properties

• Melting Point: 232-234℃
• Boiling Point: 896.3±65.0 °C at 760 mmHg
• Flash Point: 495.9±34.3 °C
• Appearance: /
• Density: 1.56
• PKA: 12.52±0.70(Predicted)
• CAS DataBase Reference: 7,10-Bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III(CAS DataBase Reference)
• NIST Chemistry Reference: 7,10-Bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III(95603-44-4)
• EPA Substance Registry System: 7,10-Bis-O-(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin III(95603-44-4)

Safety Data

• Hazardous Substances Data: 95603-44-4(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 32981-86-5 10-deacetylbaccatin III 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 67-56-1 methanol 

Downstream Products

• 186371-27-7 C₅₀H₅₅Cl₆NO₁₇ 
• 204580-15-4 13-[3-(2-naphthyl)propanoyl]-7,10-bis(2,2,2-trichloroethoxycarbonyl)baccatin III 
• 178247-84-2 C₄₉H₅₉Cl₆NO₁₈ 
• 186596-01-0 C₅₁H₄₉Cl₆NO₁₆ 
• 709038-54-0 C₅₁H₄₉Cl₆NO₁₆ 
• 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 
• 1452586-11-6 13-O-((2S,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 
• 174729-12-5 13-O-((2R,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin 
• 859498-31-0 C₅₇H₆₁Cl₆NO₁₉ 
• 174847-58-6 C₄₄H₄₄Cl₆O₁₆ 
• 171251-33-5 7,10-bis-O-(2,2,2,-trifluoroethoxycarbonyl)-13-O-[(3S)-3-(tert-butoxycarbonylamino)-2,2-difluoro-3-(2-furyl)propionyl]-10-deacetylbaccatin III 
• 1053730-90-7 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)-13-O-{3-(tert-butoxycarbonylamino)-3-[(1-tert-butoxycarbonyl)pyrrole-2-yl]-2,2-difluoropropionyl}-10-deacetylbaccatin III 

Relevant articles and documents

Preparation method of cabazitaxel

The invention discloses a preparation method of cabazitaxel, which comprises the following specific steps: dissolving 10-deacetylbaccatin III with dichloromethane and pyridine, dropwise adding 2,2,2-trichloroethyl chloroformate, and treating to obtain an intermediate I; mixing toluene, 4-dimethylaminopyridine, the intermediate I and (4S,5R)-3-tert-butoxycarbony-2-(4-anisy)- 4-phenyl-5-oxazolidinecarboxylic acid, stirring, dropwise adding N,N'-dicyclohexylcarbodiimide, and stirring for reaction to obtain an intermediate II; dissolving the intermediate II with ethyl acetate and acetic acid, adding zinc powder, carrying out a stirring reaction to obtain an intermediate III, dissolving the intermediate III with dichloromethane, adding 1,8-bis(dimethylamino)naphthalene, a molecular sieve and trimethyloxonium tetrafluoroborate, and carrying out a stirring reaction to obtain an intermediate IV; dissolving and clarifying the intermediate IV with methanol, dropwise adding a hydrochloric acid methanol solution having a concentration of 1mol/L, and stirring for reaction to obtain cabazitaxel. According to the method, methylation can be realized at room temperature, the product purity is good, the yield is high, starting materials are easy to obtain, and large-scale preparation can be carried out.

Method for synthesizing cabazitaxel from 10-deacetylbaccatin III

The invention discloses a method for synthesizing cabazitaxel from 10-deacetylbaccatin III. According to the method, 10-deacetylbaccatin III is used as a raw material, and 7,10-(di)Troc-10-DAB is prepared in the presence of a solvent, a catalyst and chloroformic acid 2, 2, 2-trichloroethyl ester; then 7,10-(di)Troc-10-DAB is condensed with a side chain of docetaxel to prepare an intermediate II, the intermediate II is subjected to protective group removal to obtain a kappa precursor I, the kappa precursor I is further prepared into a kappa precursor II, the kappa precursor II is subjected to sulfur methyl removal, and then is hydrolyzed under acidic conditions to obtain crude cabazitaxel; the crude cabazitaxel is subjected to recrystallization, column chromatography, recrystallization andpurification to obtain the cabazitaxel with the content being greater than 99%. The method provided by the invention has the advantages that the reaction conditions are mild and controllable, some ofthe reactions can be carried out in one pot, a methylation reagent used is a non-toxic reagent, and is safe, reliable, low in cost and high in yield, and the obtained product is high in purity, less in impurity content, and suitable for industrial production and marketing applications.

Method for preparing 7,10-dichloro-ethoxymethyl chloride-10-deacetylbaccatin III by using microchannel reactor

The invention provides a method for preparing 7,10-dichloro-ethoxymethyl chloride-10-deacetylbaccatin III by using a microchannel reactor. According to the invention, a selective esterification reaction is carried out in the microchannel reactor with inlets and an outlet, the method comprises the following steps: S1) preparing 10-deacetylbaccatin III source liquid and chloro-carbonic acid-2,2,2-trichloro ethyl ester source liquid, S2) conveying the 10-deacetylbaccatin III source liquid and chloro-carbonic acid-2,2,2-trichloro ethyl ester source liquid into two inlets of the microchannel reactor through a transfer pump; and S3) passing two source liquid through a mixing module and a reaction module in order, performing the selective esterification reaction, controlling the temperature of the mixing module and the reaction module being 25-50 DEG C, wherein the stay time is 30-120.6 s, and flowing a reaction solution out from the outlet. The method employs the microchannel reactor for synthesis of the 7,10-dichloro-ethoxymethyl chloride-10-deacetylbaccatin III, which solves the problems of long synthesis time, low yield and complex operation of the 7,10-dichloro-ethoxymethyl chloride-10-deacetylbaccatin III.