153652-75-6

Upstream product

• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 124605-42-1 methyl (2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropionate 
• 158830-39-8 methyl (2S,3S)-2-hydroxy-3-(N-tert-butoxycarbonylamino)-3-phenylpropanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 322407-45-4 (+)-(2S,3R)-methyl 3-amino-2-hydroxy-3-phenylpropanoate 
• 161759-90-6 (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 147058-27-3 methyl (2R,3S)-2-hydroxy-3-phenyl-3-<(S)-1-methylbenzylamino>propanoate 
• 157240-36-3 (2R,3S)-3-phenylisoserine methyl ester 

Downstream Products

• 859498-31-0 C₅₇H₆₁Cl₆NO₁₉ 

Relevant academic research and scientific papers

Synthetic method of docetaxel side chain

The invention relates to a synthetic method of a docetaxel side chain, which comprises the following steps: by using (2R, 3S)-2-hydroxy-3-phenyl-3-(((S)-1-phenethyl)-amino)methyl propionate as a raw material, carrying out reduction reaction in the presence of palladium on carbon and hydrogen to obtain (2R, 3S)-3-phenyl isoserine methyl ester salt, and carrying out di-tert-butyl dicarbonate substitution reaction to obtain (2R, 3S)-3-t-butyloxycarboryl-2-hydroxy-3-Methyl 3-phenylpropionate; preparing (4S, 5R)-3-tert-butoxycarbonyl-2-(4-methoxy phenyl)-4-phenyl-5-oxazoline carboxylic acid methylester from through cyclization protection reaction, and finally hydrolyzing to obtain a docetaxel side chain crude product; and recrystallizing the crude product of the docetaxel side chain, and further purifying to obtain a finished product of the docetaxel side chain. The synthetic method disclosed by the invention is safe, environment-friendly, economical, efficient and suitable for large-scaleindustrial 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.

NOVEL AMINO ACID MOLECULE AND USES THEREOF

There is provided novel amino acid molecules and processes for their preparation. There is also provided novel amino acid molecules and their use in processes for preparing the compounds that are useful for the synthesis of paclitaxel, and docetaxel, the anticancer drug.

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.

A novel method to synthesize docetaxel and its isomer with high yields

Side chains of docetaxel and its isomer were obtained through Staudinger cycloaddition and catalytic hydrogenation of chlorophenyl intermediates, using chlorobenzaldehyde as starting material. Syntheses of three novel chiral azetidinone derivatives through the Staudinger cycloaddition reaction of chlorophenyl chiral amine Schiff base with different substituted positions were described and their ring-opening reaction under the catalysis of Pd/MgCO 3 or Pd/C to afford side chains of docetaxel and its isomer in high yields was investigated. Finally, docetaxel and its isomer were obtained. Single crystal of (3S,4R)-3-hydroxy-N-[(S)(1-phenyl)ethyl]-4 -(2′-chlorophenyl) -2-azetidinone (4c) was obtained, the configuration of which was determined by X-ray diffraction. Because of the mild cyclization reaction condition and convenient asymmetric resolution operation when p-chlorobenzaldehyde was employed instead of benzaldehyde, the yield of cyclization and hydrogenation increased dramatically and the total yield of docetaxel was higher than the result in literature. When o-chlorobenzaldehyde was employed instead of benzaldehyde an isomer of docetaxel was obtained by the same way.

Taxoids, preparation thereof, and pharmaceutical compositions containing same

Novel taxoids of general formula (I), wherein R is a substituted alkyl radical or an alkenyl, alkynyl, cycloalkyl, optionally substituted cycloalkenyl or phenyl radical, or an aromatic 5- or 6-membered heterocyclic radical; and Z is a hydrogen atom or a radical of general formula (II), wherein R1 is an optionally substituted benzoyl, thenoyl or furoyl radical or a radical R2 --O--CO, where R2 is an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, optionally substituted phenyl, or heterocycl radical, and R3 is an aromatic heterocyclic, alkyl, alkenyl, alkynyl cycloalkyl, phenyl or naphthyl radical. The novel products of general formula (I), wherein Z is a radical of general formula (II), have remarkable antitumoral activity. STR1

Process for preparing taxane derivatives

Method of preparing taxane derivatives of general formula (I) by esterification of protected baccatine III or 10-deacetyl-baccatine III by means of an acid of general formula (VII), deprotection of the side chain and elimination of the hydroxy function protection groupings. In general formulae (I) and (VII): Ar stands for aryl, R is hydrogen or acetyl, R1 is benzoyl or R2 --O--CO-- in which R2 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, bicycloalkyl, phenyl or heterocyclyl, and R3 is hydrogen, alkoxy, optionally substituted aryl. STR1

2-Monosubstituted-1,3-Oxazolidines as Improved Protective Groups of N-Boc-Phenylisoserine in Docetaxel Preparation

A new route for semisynthetic docetaxel, 1, is desribed using 2-monosubstituted-4-phenyl-1,3-oxazolidine-5-carboxylic acids in esterification of 7,10-O-diTroc-10-desacetylbaccatin III (4).Subsequent deprotection of esters 10(+10') afforded title compound 1 without removal of the Boc group.