143615-00-3

Basic information

• Product Name: (2R,3S)-3-Phenylisoserine ethyl ester
• Synonyms: Cabazitaxel Impurity 24 ( (2R,3S)-3-Amino-2-hydroxy-3-phenylpropionic Acid Ethyl Ester)
• CAS NO: 143615-00-3
• Molecular Formula: C11H15NO3
• Molecular Weight: 209
• Mol File: 143615-00-3.mol
• Article Data: 11

Chemical Properties

• Melting Point: 82-84℃
• Boiling Point: 355.3±42.0 °C(Predicted)
• Appearance: /
• Density: 1.178
• PKA: 10.48±0.45(Predicted)
• CAS DataBase Reference: (2R,3S)-3-Phenylisoserine ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-Phenylisoserine ethyl ester(143615-00-3)
• EPA Substance Registry System: (2R,3S)-3-Phenylisoserine ethyl ester(143615-00-3)

Safety Data

• Hazardous Substances Data: 143615-00-3(Hazardous Substances Data)

Usage

Description

(2R,3S)-3-Phenylisoserine ethyl ester is an organic compound with the molecular formula C11H15NO3. It is a white solid and is known for its role as a key reactant in the synthesis of important pharmaceutical compounds, specifically Taxotere and Taxol side chains. This chiral compound is characterized by its specific stereochemistry, with the R configuration at the 2nd carbon and the S configuration at the 3rd carbon.

Uses

Used in Pharmaceutical Industry:
(2R,3S)-3-Phenylisoserine ethyl ester is used as a reactant for the preparation of Taxotere and Taxol side chains. These are crucial components in the synthesis of the anticancer drugs Taxol (paclitaxel) and Taxotere (docetaxel), which are widely used in the treatment of various types of cancer, including breast, ovarian, and lung cancer. The compound's role in the production of these life-saving drugs highlights its importance in the pharmaceutical industry.

Upstream product

• 121-39-1 ethyl cis-3-phenylglycidate 
• 129939-62-4 (2S,3R)-3-Azido-2-hydroxy-3-phenyl ethyl propanoate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 41381-97-9 ethyl 2-chloro-3-oxo-3-phenylpropionate 
• 1333321-07-5 (2R,3S)-ethyl 2-acetoxy-3-((4-methoxyphenyl)amino)-3-phenylpropanoate 
• 1333320-89-0 ethyl 2-acetoxy-3-(4-methoxyphenylamino)-3-phenylacrylate 
• 1254708-85-4 methyl 2-hydroxy-3-(4-methoxyphenylamino)-3-phenylpropanoate 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 100-52-7 benzaldehyde 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 481054-46-0 ethyl (2RS,3SR)-3-amino-2-hydroxy-3-phenylpropionate 
• 64-17-5 ethanol 
• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 

Downstream Products

• 132201-32-2 (2R,3S)-3-phenylisoserine hydrochloride 
• 155396-65-9 (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid 
• 1395491-92-5 (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropionic acid ethyl ester 
• 153433-80-8 ethyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 143527-75-7 (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine 
• 143527-76-8 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 143527-73-5 C₅₁H₆₀Cl₃NO₁₇ 

Relevant articles and documents

Utilization of (18-Crown-6)-2,3,11,12-tetracarboxylic Acid as a Chiral NMR Solvating Agent for Diamines and β-Amino Acids

The compound (18-crown-6)-2,3,11,12-tetracarboxylic acid was evaluated as a chiral nuclear magnetic resonance (NMR) solvating agent for a series of diamines and bicyclic β-amino acids. The amine must be protonated for strong association with the crown ether. An advantage of (18-crown-6)-2,3,11,12-tetracarboxylic acid over many other crown ethers is that it undergoes a neutralization reaction with neutral amines to form the protonated species needed for binding. Twelve primary diamines in neutral and protonated forms were evaluated. Diamines with aryl and aliphatic groups were examined. Some are atropisomers with equivalent amine groups. Others have two nonequivalent amine groups. Association equilibria for these systems are complex, given the potential formation of 2:1, 1:1, and 1:2 crown-amine complexes and given the various charged species in solution for mixtures of the crown ether with the neutral amine. The crown ether produced enantiomeric differentiation in the 1H NMR spectrum of one or more resonances for every diamine substrate. Also, a series of five bicyclic β-amino acids were examined and (18-crown-6)-2,3,11,12-tetracarboxylic acid caused enantiomeric differentiation in the 1H NMR spectrum of three or more resonances of each compound. Chirality 27:708-715, 2015.

Rhodium-catalyzed enantioseletive hydrogenation of tetrasubstituted α-acetoxy β-enamido esters: A new approach to chiral α-hydroxyl-β-amino acid derivatives

Asymmetric hydrogenation of tetrasubtitued α-acetoxy β-enamido esters with rhodium catalysts based on chiral diphosphine ligands provides an efficient and concise route to the synthesis of chiral α-hydroxyl-β-amino acid derivatives in excellent enantioselectivities. The products are valuable chiral building blocks in many biologically active compounds and have important applications in organic synthesis.

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