859498-31-0

Basic information

• Product Name: 3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,...
• CAS NO: 859498-31-0
• Molecular Formula: C₅₇H₆₁Cl₆NO₁₉
• Molecular Weight: 1276.82
• Mol File: 859498-31-0.mol

Chemical Properties

• CAS DataBase Reference: 3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,...(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,...(859498-31-0)
• EPA Substance Registry System: 3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,...(859498-31-0)

Safety Data

• Hazardous Substances Data: 859498-31-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,... is used as a pharmaceutical compound for its potential therapeutic properties. 3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,...'s unique structure and functional groups may contribute to its ability to interact with biological targets and pathways, making it a promising candidate for the development of new drugs and therapies.
Used in Materials Science:
3,5-Oxazolidinedicarboxylic acid, 2-(4-methoxyphenyl)-4-phenyl-, 5-[(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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,... is used as a component in the development of advanced materials. Its unique structure and functional groups may enable the creation of new materials with specific properties, such as improved strength, flexibility, or chemical resistance, making it valuable in various applications, including coatings, adhesives, and composites.

Upstream product

• 670254-71-4 (2*,4S,5R)-methyl N-tert-butoxycarbonyl-2-(4'-methoxy)phenyl-4-phenyl-1,3-oxazolidine-5-methionate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 
• 32981-86-5 10-deacetylbaccatin III 
• 95603-44-4 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III 
• 196404-55-4 acide (4S,5R)-N-(tert-butoxycarbonyl)-2-(4-O-methoxyphenyl)-4-phenyl-5-oxazolidine carboxylique 
• 949459-78-3 (4S,5S)-3-(tert-butoxycarbonyl)-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid 

Downstream Products

• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 183133-96-2 carbazitaxel 

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.

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.

Docetaxel side chain 2'-derived novel taxanes antitumor compound as well as synthesis method and application thereof

The invention discloses a docetaxel side chain 2'-derived novel taxanes antitumor compound shown as the general structure formula (I) as well as a synthesis method and application thereof. In the formula, X is N or O, R is H or acetyl, and R' is H, nitryl, cyano, methoxyl or a halogen group. The synthesis method takes 10-deacetylbaccatin is used as a raw material; after 7-OH and 10-OH are protected, condensation with phenylisoserine (side chain) protecting 3'-NHBoc and 2'-OH in the presence of condensation agents DCC (Dicyclohexylcarbodiimide) and DMAP (Dimethylaminopyridine) is performed; esterification with substituted phenyl isoxazole carboxylic acid or substituted phenyl oxadiazole methyl carboxylic acid in the presence of the DCC and the DMAP is performed; finally, a protecting group is removed to obtain the compound. The compound disclosed by the invention has relatively high activity on tumor cells.

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.

Dynamic kinetic resolution of α-chloro β-keto esters and phosphonates: Hemisynthesis of Taxotere through Ru-DIFLUORPHOS asymmetric hydrogenation

The dynamic kinetic resolution (DKR) of racemic α-chloro β-ketoesters and α-chloro β-ketophosphonates through ruthenium-mediated asymmetric hydrogenation is reported. The corresponding α-chloro β-hydroxyesters and α-chloro β- hydroxyphosphonates were obtained in good to high enantio- and diastereomeric excesses using, in particular, the atropisomeric ligand DIFLUORPHOS. This methodology allowed an efficient preparation of the anti phenylisoserine side chain of Taxotere which has been used for the hemisynthesis of the cancer therapeutic agent itself. In addition, 13C NMR in chiral oriented solvents was used to investigate the DKR effect.