153433-80-8

Basic information

• Product Name: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER
• Synonyms: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER;Ethyl (2R,3S)-3-(benzoylamino)-2-hydroxybenzenepropanoate;(αR,βS)-β-(BenzoylaMino)-α-hydroxybenzenepropanoic Acid Ethyl Ester;TAXOL SIDE CHAIN ETHYL ESTER(SH);Ethyl(2R,3S)-3-(benzoylaMino)-2-hydroxybenzenepropanoale;BENZYLOXYPHENYLISOSERINE ETHYLESTER,N-(P);(2R,3S)- Phenylisoserine ethylester;Benzenepropanoic acid, b-(benzoylamino)-a-hydroxy-, ethyl ester, (aR,bS)-
• CAS NO: 153433-80-8
• Molecular Formula: C₁₈H₁₉NO₄
• Molecular Weight: 313.35
• EINECS: 1806241-263-5
• Product Categories: Amino Acids & Derivatives;Anti-virals;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 153433-80-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 162～163℃
• Boiling Point: 546.8±50.0 °C(Predicted)
• Appearance: /
• Density: 1.211±0.06 g/cm3(Predicted)
• Solubility: Chloroform, Ethyl Acetate, Methanol
• PKA: 12.19±0.20(Predicted)
• CAS DataBase Reference: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER(153433-80-8)
• EPA Substance Registry System: (2R,3S)-3-PHENYLISOSERINE ETHYLESTER(153433-80-8)

Safety Data

• Hazardous Substances Data: 153433-80-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(2R,3S)-3-PHENYLISOSERINE ETHYLESTER is an intermediate in the preparation of potent anticancer drug Paclitaxel (P132500) used to study the location of the binding sites. (2R,3S)-3-PHENYLISOSERINE ETHYLESTER shows cytotoxic, antiviral and immunomodulatory activity.

Upstream product

• 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 
• 7352-07-0 N-benzoyl-α-phenylglycine 
• 98-88-4 benzoyl chloride 
• 2935-35-5 (S)-2-phenylglycine 
• 4192-77-2 ethyl cinnamate 
• 163893-33-2 ethyl (2R,3S)-3-azido-2-benzoyloxy-3-phenylpropionate 
• 163960-83-6 (4S,5R)-2,2-Dioxo-5-phenyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 
• 163893-32-1 (4S,5R)-2-Oxo-5-phenyl-2λ⁴-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 

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 articles and documents

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