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

Description

(2R,3S)-3-PHENYLISOSERINE ETHYLESTER is an organic compound with the molecular formula C10H13NO2. It is a white solid and is known for its significant role in the pharmaceutical industry due to its various biological activities and applications.

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

• 153433-79-5 2-keto-3-(N-benzoyl-amino)-3-phenyl propionic acid ethyl ester 
• 153433-82-0 anti-(2S,3S)-(-)-N-benzoyl-3-phenylisoserine ethyl ester 
• 246861-68-7 ethyl (2R,3S)-3-azido-2-O-benzoyl-3-phenylpropionate 
• 869012-73-7 ethyl (4S,5R)-2,4-diphenyl-4,5-dihydrooxazole-5-carboxylate 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 98-88-4 benzoyl chloride 
• 860646-95-3 ethyl (2R,3S)-3-{[(R)-1-phenylethyl]amino}-2-hydroxy-3-phenylpropanoate 
• 56941-77-6 (R)-1-phenylethyl(benzylidene)amine 
• 100-52-7 benzaldehyde 
• 41381-97-9 ethyl 2-chloro-3-oxo-3-phenylpropionate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 100-47-0 benzonitrile 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 146452-39-3 (2S,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate 

Downstream Products

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

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%).

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