153433-80-8

Usage

Uses

Used in Pharmaceutical Industry:
(2R,3S)-3-PHENYLISOSERINE ETHYLESTER is used as an intermediate in the preparation of the potent anticancer drug Paclitaxel (P132500). It plays a crucial role in studying the location of the binding sites, which helps in understanding the drug's mechanism of action and improving its efficacy.
Used in Anticancer Applications:
(2R,3S)-3-PHENYLISOSERINE ETHYLESTER is used as a cytotoxic agent, exhibiting potential in the treatment of various types of cancer. Its cytotoxic properties make it a valuable compound in the development of new anticancer drugs and therapies.
Used in Antiviral Applications:
(2R,3S)-3-PHENYLISOSERINE ETHYLESTER is used as an antiviral agent, showing potential in the development of new treatments for viral infections. Its antiviral activity makes it a promising candidate for further research and development in the field of virology.
Used in Immunomodulatory Applications:
(2R,3S)-3-PHENYLISOSERINE ETHYLESTER is used as an immunomodulatory agent, which can help regulate the immune system and potentially be used in the treatment of various immune-related disorders. Its immunomodulatory activity highlights its potential in the development of new therapies for autoimmune diseases and other immune system-related conditions.

Upstream product

• 153433-82-0 anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 98-88-4 benzoyl chloride 
• 153433-79-5 2-keto-3-(N-benzoyl-amino)-3-phenyl propionic acid ethyl ester 
• 153524-49-3 1-benzamido-3-ethoxy-3-oxo-1-phenylprop-1-en-2-yl ethyl oxalate 
• 246861-68-7 ethyl (2R,3S)-3-azido-2-O-benzoyl-3-phenylpropionate 
• 623-73-4 diazoacetic acid ethyl ester 
• 10374-29-5 N-benzylidenebenzamide 
• 121-39-1 ethyl 3-phenylglycidate 
• 2272-55-1 (2R,3S)-ethyl 3-phenylglycidate 
• 14904-52-0 ethyl 2-acetoxy-3-oxo-3-phenylpropanoate 
• 98-86-2 acetophenone 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 1333321-07-5 (2R,3S)-ethyl 2-acetoxy-3-((4-methoxyphenyl)amino)-3-phenylpropanoate 

Downstream Products

• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 182615-45-8 (4S-trans)-3-benzoyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid ethyl ester 
• 153433-82-0 anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester 

Relevant academic research and scientific papers

N-benzoyl phenylisoserine derivative as well as synthesis method and application thereof

The invention discloses an N-benzoyl phenylisoserine derivative and a synthesis method thereof. N-benzoyl phenylimine, a diazo compound and isopropyl aldehyde are taken as raw materials, a molecular sieve is taken as a water absorbing agent, rhodium aceta

Catalytic Asymmetric Epoxidation of Aldehydes with Two VANOL-Derived Chiral Borate Catalysts

A highly diastereo- and enantioselective method for the epoxidation of aldehydes with α-diazoacetamides has been developed with two different borate ester catalysts of VANOL. Both catalytic systems are general for aromatic, aliphatic, and acetylenic aldehydes, giving high yields and inductions for nearly all cases. One borate ester catalyst has two molecules of VANOL and the other only one VANOL. Catalysts generated from BINOL and VAPOL are ineffective catalysts. An application is shown for access to the side-chain of taxol.

Bioresolution production of (2R,3S)-Ethyl-3-phenylglycidate for chemoenzymatic synthesis of the taxol C-13 side chain by galactomyces geotrichum ZJUTZQ200, a new epoxide-hydrolase-producing strain

A newly isolated Galactomyces geotrichum ZJUTZQ200 strain containing an epoxide hydrolase was used to resolve racemic ethyl 3-phenylglycidate (rac-EPG) for producing (2R,3S)-ethyl-3-phenylglycidate ((2R,3S)-EPG). G. geotrichum ZJUTZQ200 was verified to be able to afford high enantioselectivity in whole cell catalyzed synthesis of this chiral phenylglycidate synthon. After the optimization of the enzymatic production and bioresolution conditions, (2R,3S)-EPG was afforded with high enantioselectivity (e.e.S > 99%, E > 49) after a 8 h reaction. The co-solvents, pH buffer solutions and substrate/cell ratio were found to have significant influences on the bioresolution properties of G. geotrichum ZJUTZQ200. Based on the bioresolution product (2R,3S)-EPG, taxol's side chain ethyl (2R,3S)-3-benzoylamino-2-hydroxy- 3-phenylpropionate was successfully synthesized by a chemoenzymatic route with high enantioselectivity (e.e.S > 95%).

Chemo- and biocatalytic strategies to obtain phenylisoserine, a lateral chain of Taxol by asymmetric reduction

Enriched ethyl 3-benzamido-2-hydroxy-3-phenylpropanoate (protected phenylisoserine), the chiral side chain of Taxol, was obtained via asymmetric reduction with transition metal-diphoshine complexes or with whole cells of non-conventional yeasts. Asymmetri

Highly diastereoselective and enantioselective synthesis of α-hydroxy β-amino acid derivatives: Lewis base catalyzed hydrosilylation of α-acetoxy β-enamino esters

By design: A series of α-acetoxy-β-enamino esters 1 were synthesized and then subjected to catalytic asymmetric hydrosilylation. In the presence of a chiral Lewis base catalyst, the reactions proceeded smoothly to provide a wide range of chiral α-acetoxy β-amino acid derivatives in high yields with good diastereoselectivities and enantioselectivities. Copyright

1,3-dipolar cycloadditions of carbonyl ylides to aldimines: Scope, limitations and asymmetric cycloadditions

The development of a diastereoselective 1,3-dipolar cycloaddition of carbonyl ylides and imines for the synthesis of α-hydroxy-β-amino esters is described. The methodology is successfully applied to chiral α-methylbenzylimines affording enantiomerically p

Asymmetric epoxidation of cis-alkenes with arabinose-derived ketones: enantioselective synthesis of the side chain of Taxol

The ee values of asymmetric epoxidation of cis-ethyl cinnamate 15 with arabinose-derived ketones as catalyst and Oxone as the terminal oxidant were found to increase inversely with the size of the catalyst acetal blocking group. Ketone catalyst

A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: Key intermediates for taxol side chain and phenylnorstatine

Starting from the bromination of α-ketoesters to obtain 3-bromo-2-oxoalkanoates and bioreduction with Saccharomyces cerevisiae entrapped in calcium alginate pellets with double gel layers, syn-(2R,3S)-β-bromo- α-hydroxy esters were obtained regioselectively in high yields and high ee. These chiral bromohydrins were cyclized to epoxides that were transformed into oxazolidines and finally opened by acidic hydrolysis to give syn-(2S,3S)-β-amino-α-hydroxy esters in high overall yields and high ee. The enantiomeric excesses of all the intermediates were maintained during the reaction sequence.

Enantiodivergent, biocatalytic routes to both taxol side chain antipodes

Two enantiocomplementary bakers' yeast enzymes reduced an α-chloro-β-keto ester to yield precursors for both enantiomers of the N-benzoyl phenylisoserine Taxol side chain. After base-mediated ring closure of the chlorohydrin enantiomers, the epoxides were

1,3-Dipolar cycloadditions of carbonyl ylides to aldimines: A three-component approach to syn-α-hydroxy-β-amino esters

(Chemical Equation Presented) A highly diastereoselective Rh II-catalyzed 1,3-dipolar cycloaddition leads to the formation of syn-β-amino alcohols and syn-α-hydroxy-β-amino acids in high yields (see scheme; p-TSA = poro-toluenesulfonic acid, Bn = benzyl). This three-component approach to the addition of metal-associated carbonyl ylides to aldimines was applied to a short enantioselective synthesis of the C13 side chain of taxol.