114915-20-7

Basic information

• Product Name: 7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.
• Synonyms: Benzenepropanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxy-, 12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester
• CAS NO: 114915-20-7
• Molecular Formula: C₄₃H₅₃NO₁₄
• Molecular Weight: 807.88
• Mol File: 114915-20-7.mol
• Article Data: 62

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.(CAS DataBase Reference)
• NIST Chemistry Reference: 7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.(114915-20-7)
• EPA Substance Registry System: 7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.(114915-20-7)

Safety Data

• Hazardous Substances Data: 114915-20-7(Hazardous Substances Data)

Upstream product

• 196404-55-4 acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique 
• 1568962-20-8 C₅₃H₇₅NO₁₄Si 
• 1568962-15-1 C₄₇H₆₃NO₁₄Si 
• 1354900-66-5 4α-acetoxy-2α-benzoyloxy-5β,20-epoxy-1β,13α-dihydroxy-7β,10β-dimethoxy-9-oxo-11-taxen-13α-yl (2R,4S,5S)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate 
• 1227402-71-2 7,10-di-troc-N'-Boc-2'-acetyldocetaxel 
• 1219592-94-5 (2R,3S)-N,N-di-Boc-2-acetyl-3-phenylisoserine 
• 1219592-93-4 (2R,3S)-N,N-di-Boc-2-acetyl-3-phenylisoserine benzyl ester 
• 1219592-92-3 (2R,3S)-N-Boc-2-acetyl-3-phenylisoserine benzyl ester 
• 1219592-76-3 (2R,3S)-N-Boc-3-phenylisoserine benzyl ester 
• 145514-62-1 RPR 130523 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 632335-31-0 7,10-di-O-(2-chlroacetyl)docetaxel 
• 500726-10-3 7,10-di-O-chloroacetyl-10-deacetylbaccatin III 
• 159262-93-8 10-deacetylbaccatin III-13-O-[(4S,5R)-4-phenyl-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidine-5-carboxylate] 

Downstream Products

• 262598-45-8 2',10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 148408-66-6 N-tert-butoxycarbonyl-10-deacetyl-N-debenzoyl-taxol trihydrate 
• 1068633-26-0 docetaxel/mono propylene glycol clathrate 
• 1568962-15-1 C₄₇H₆₃NO₁₄Si 
• 1568962-20-8 C₅₃H₇₅NO₁₄Si 

Relevant articles and documents

Biological evaluation of new antitumor taxoids: Alteration of substitution at the C-7 and C-10 of docetaxel

A series of new docetaxol analogues have been designed and synthesized. And their cytotoxicities against cancer cells have been evaluated by MTT method. Most of these compounds showed selective inhibitions on human cancer cell lines. Among them, compound 8 exhibited higher inhibitory activity than Paclitaxel (Taxol) against several cancer cell lines. This work indicated that appropriate modification at C-7 and C-10 of docetaxel might be a promising approach for this unique class of anticancer compounds.

Synthesis of Taxol and Docetaxel by Using 10-Deacetyl-7-xylosyltaxanes

A mixture of taxols was prepared from 10-deacetyl-7-xylosyltaxanes by three-step reactions: redox, acetylation, and deacetylation. The mixture was separated by column chromatography on silica gel to afford Taxol, Taxol B (Cephalomannine) and Taxol C. The mixture of Taxol B and Taxol C was converted to Docetaxel by Schwartz's reagent. The structures of Taxol and Docetaxel were characterized by HPLC, 1H-NMR, 13C-NMR and MS. This synthetic process has expanded the source of biomass for the chemical semi-synthesis of Taxol and Docetaxel, reduced the production costs, and increased the biomass resource of taxanes.

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.