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

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

• 24424-99-5 di-tert-butyl dicarbonate 
• 133524-69-3 C₃₈H₄₅NO₁₂ 
• 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 
• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 32981-86-5 10-deacetylbaccatin III 
• 196404-55-4 acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique 
• 1021489-55-3 SPT₁₁₄₁ M₆ 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 143527-74-6 ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 143527-75-7 (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine 
• 100-52-7 benzaldehyde 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 

Downstream Products

• 144654-55-7 C₄₃H₅₃NO₁₄ 
• 162784-72-7 7-epi-10-carbonyl docetaxel 
• 162784-72-7 10-oxodocetaxel 
• 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 
• 262598-45-8 2',10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 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.

Taxotere by esterification with stereochemically 'wrong' (2S,3S)- phenylisoserine derivatives

Cyclically protected anti (2S,3S) phenylisoserines on esterification with baccatin III derivatives afford Taxotere and taxol precursors with the syn (2'R, 3'S) side chain.

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.

Formulation optimization of an ephrin A2 targeted immunoliposome encapsulating reversibly modified taxane prodrugs

Ephrin A2 targeted immunoliposomes incorporating pH-sensitive taxane prodrugs were developed for sustained delivery of active drug to solid tumors. Here we describe the systematic formulation development and characterization of these immunoliposomes. We s

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 purifying docetaxel

The invention discloses a method for purifying docetaxel. A docetaxel solid precipitates from a dichloromethane and toluene mixed solution. The purifying method has the advantages of great reduction of the single content of every impurity in docetaxel, introduction of few impurities, improvement of the purity of the product, and high yield, and is very suitable for industrial large-scale production, and the obtained product meets preparation demands, and can be directly used to prepare a docetaxel injection.

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.

Synthesis method of docetaxel

The invention provides a synthesis technology of docetaxel. The synthesis technology comprises the following steps: with double-protection 10-DAB of a structure shown as a formula I as a raw material,performing condensation reaction between the double-pro

Method for semisynthesis of Docetaxel and intermediate of Docetaxel

The invention relates to a method for semisynthesis of Docetaxel and an intermediate of the Docetaxel. The method provided by the invention comprises the steps of firstly, carrying out hydroxyl protection on C7 and C10 of 10-DAB III (10-deacetylbaccatin III) by using 2,2,2-trichloroethylchloroformate so as to obtain an intermediate I, subjecting the intermediate I to a reaction with a side chain radical compound so as to prepare an intermediate II, subjecting the intermediate II to a hydrogenation reaction under the catalysis of palladium-charcoal so as to prepare an intermediate III, subjecting the intermediate III to a reaction under acidic conditions so as to obtain a Docetaxel crude product, and subjecting the Docetaxel crude product to purification, thereby obtaining a purified product. According to the method provided by the invention, the 10-DAB III raw material can be sufficiently utilized, finally-produced byproducts are few, the final product Docetaxel has the purity of 99.6% to 99.9%, the mole yield reaches up to 73% to 82%, and the utilization ratio of the 10-DAB III can be greatly increased.

EPHRIN RECEPTOR A2 (EPHA2)-TARGETED DOCETAXEL-GENERATING NANO-LIPOSOME COMPOSITIONS

EphA2-targeted immunoliposomes for delivering docetaxel are useful in the treatment of certain types of cancer. The immunoliposomes can include an EphA2 targeting moiety (e.g., a scFv) and encapsulate a docetaxel prodrug in a stable salt form within a liposome having an average size of about 100 nm. Novel docetaxel prodrugs suitable for loading into nanoliposomes (including immunoliposomes) are provided, along with novel and other useful EphA2 targeting moieties for preparation of EphA2-targeted doxorubicin-generating immunoliposome therapies. Pharmaceutical compositions can be prepared that include nanoliposomes encapsulating one or more docetaxel prodrugs, and/or immunoliposomes or nanoparticles comprising an EphA2 binding moiety and encapsulating one or more docetaxel prodrugs. The pharmaceutical compositions are useful for administration to a patient for the treatment of cancer.