114977-29-6

Basic information

• Product Name: 2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol
• Synonyms: 2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol
• CAS NO: 114977-29-6
• Molecular Weight: 807.892
• Mol File: 114977-29-6.mol
• Article Data: 64

Chemical Properties

• CAS DataBase Reference: 2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol(CAS DataBase Reference)
• NIST Chemistry Reference: 2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol(114977-29-6)
• EPA Substance Registry System: 2'-epi 3'-epi N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyl taxol(114977-29-6)

Safety Data

• Hazardous Substances Data: 114977-29-6(Hazardous Substances Data)

Upstream product

• 95603-45-5 7,10-di(2,2,2-trichloroethyloxy-carbonyl)-13-cinnamoyl-10-deacetyl baccatin III 
• 95603-44-4 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 125354-16-7 10-acetyldocetaxel 
• 32981-86-5 10-deacetylbaccatin III 
• 196404-55-4 acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique 
• 151509-27-2 2'-acetyldocetaxel 
• 4248-19-5 tert-butyl carbazate 
• 100-52-7 benzaldehyde 
• 114977-25-2 C₄₉H₅₅Cl₆NO₁₈ 
• 859498-34-3 (2*,4R,5S)-N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-formic acid 
• 859498-33-2 (2*,4R,5S)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate 
• 157580-28-4 (2R,4S,5R)-2-(3,4-Dimethoxy-phenyl)-4-phenyl-oxazolidine-3,5-dicarboxylic acid 3-tert-butyl ester 5-methyl ester 
• 153652-73-4 (2R,4S,5R)-3-t-butoxycarbonyl-4-phenyl-2-(4-methoxyphenyl)-5-methoxycarbonyl-1,3-oxazolidine 

Downstream Products

• 144654-55-7 C₄₃H₅₃NO₁₄ 
• 170171-53-6 2'-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 262598-45-8 2',10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 

Relevant articles and documents

Improved protection and esterification of a precursor of the taxotere and taxol side chains

(4S,5R)-N-BOC-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a,b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere, taxol and analogs.

Semisynthesis method for docetaxel

The invention relates to a semisynthesis method for docetaxel. The semisynthesis method comprises the following steps: protecting hydroxyl groups on 7-carbon and 10-carbon on 10-DAB III by using chloroformic acid-2,2,2-trichloroethyl ester so as to obtain an intermediate I, performing a condensation reaction on the intermediate I and a five-membered ring side chain so as to obtain an intermediateII, performing ring opening on the intermediate II under the action of hydrochloric acid to remove a protecting group on the five-membered ring side chain so as to obtain an intermediate III, and removing a Troc protecting group from the intermediate III under an acidic condition so as to obtain the docetaxel. The semisynthesis method provided by the invention has the advantages of simple processroute, mild reaction conditions, fewer impurities generated in the reaction process, higher yield and stable properties of obtained intermediates, and applicability to industrial large-scale production.

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.