62075-28-9

Usage

Uses

Used in Pharmaceutical Industry:
(2S,3R)-3-PHENYLISOSERINE is used as a building block in peptide synthesis for the development of new pharmaceuticals and chemical entities. Its unique structure may contribute to the discovery of novel therapeutic agents.
Further research is needed to fully understand and explore the potential uses and properties of (2S,3R)-3-PHENYLISOSERINE.

InChI:InChI=1/C9H13NO2/c10-9(8(12)6-11)7-4-2-1-3-5-7/h1-5,8-9,11-12H,6,10H2/t8-,9-/m1/s1

Upstream product

• 90649-87-9 2-chloro-3-hydroxy-3-phenyl-propionic acid 
• 151310-06-4 2-hydroxy-3-amino-3-phenylpropionamide 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 340179-55-7 (2S,3R)-3-(dibenzylamino)-2-hydroxy-3-phenylpropanoic acid 
• 481054-46-0 ethyl (2RS,3SR)-3-amino-2-hydroxy-3-phenylpropionate 
• 340179-39-7 (2S,3R)-3-(dibenzylamino)-2-hydroxy-3-phenylpropanenitrile 
• 174023-92-8 D-dibenzylaminophenylglycinal 
• 55325-49-0 (±)-anti-3-amino-2-hydroxy-3-phenylpropanamide 
• 1566-68-3 (2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid 

Downstream Products

• 100-52-7 benzaldehyde 
• 2835-06-5 phenylglycin 
• 140408-37-3 ethyl (2R^*,3R^*)-3-phenyl-3-amino-2-hydroxypropanoate hydrochloride 

Relevant academic research and scientific papers

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.

An investigation of nitrile transforming enzymes in the chemo-enzymatic synthesis of the taxol sidechain

Paclitaxel (taxol) is an antimicrotubule agent widely used in the treatment of cancer. Taxol is prepared in a semisynthetic route by coupling the N-benzoyl-(2R,3S)-3-phenylisoserine sidechain to the baccatin III core structure. Precursors of the taxol sidechain have previously been prepared in chemoenzymatic approaches using acylases, lipases, and reductases, mostly featuring the enantioselective, enzymatic step early in the reaction pathway. Here, nitrile hydrolysing enzymes, namely nitrile hydratases and nitrilases, are investigated for the enzymatic hydrolysis of two different sidechain precursors. Both sidechain precursors, an openchain α-hydroxy-β-amino nitrile and a cyanodihydrooxazole, are suitable for coupling to baccatin III directly after the enzymatic step. An extensive set of nitrilases and nitrile hydratases was screened towards their activity and selectivity in the hydrolysis of two taxol sidechain precursors and their epimers. A number of nitrilases and nitrile hydratases converted both sidechain precursors and their epimers.

A new enzymatic strategy for the preparation of (2R,3S)-3-phenylisoserine: a key intermediate for the Taxol side chain

Burkholderia cepacia lipase PS-IM catalysed the hydrolysis of racemic ethyl 3-amino-3-phenyl-2-hydroxypropionate with excellent enantioselectivity (E >200), when the reaction was performed with added H2O as a nucleophile, in iPr2O, at 50 °C. The hydrolysis of the less reactive enantiomeric ethyl 3-amino-3-phenyl-2-hydroxypropionate with 18% HCl afforded the corresponding enantiomerically pure (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid hydrochloride, a key intermediate for the Taxol side chain.

Tachysan useful for synthesizing method for producing compd. homochiral

A method is provided for processing a solution having optical isomers to obtain a (2R,3S) target isomer:wherein P1 is H or a hydroxyl protecting group, R1 is H, an alkyl group, an olefinic group or an aromatic group, and R2 is H or R3CO, where R3 is an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group or an O-aromatic group, provided that Ris not H when Ris Ph and Pis H. The method includes passing the solution through a chromatographic stationary phase, such as S,S Whelk-O, that has a greater affinity for one of the target isomer and an optical isomer thereof. A portion of the solution with the target isomer is then collected. The solution may be a racemic mixture of (±)-N-CBZ-3-phenylisoserine ethyl ester.

First one-pot copper-catalyzed synthesis of α-hydroxy-β-amino acids in water. A new protocol for preparation of optically active norstatines

α-Hydroxy-β-amino acids were synthesized with excellent yields for the first time in water and by a simple procedure based on a copper catalytic cycle, which included the recovery and reuse of the catalyst and is possible to realize by using only water as reaction medium.

Chiral resolution method for producing compounds useful in the synthesis of taxanes

A method is provided for processing a solution having optical isomers to obtain a (2R,3S) target isomer: wherein P1 is H or a hydroxyl protecting group, R1 is H, an alkyl group, an olefinic group or an aromatic group, and R2 is H or R3CO, where R3 is an alkyl group, an olefinic group, an aromatic group, an O-alkyl group, an O-olefinic group or an O-aromatic group, provided that R1 is not H when R3 is Ph and P1 is H. The method includes passing the solution through a chromatographic stationary phase, such as S,S Whelk-O, that has a greater affinity for one of the target isomer and an optical isomer thereof. A portion of the solution with the target isomer is then collected. The solution may be a racemic mixture of (±)-N-CBZ-3-phenylisoserine ethyl ester.

Stereoselective cyanation of chiral α-amino aldehydes by reaction with Nagata's reagent: A route to enantiopure β-amino-α-hydroxy acids

Chiral α-dibenzylamino aldehydes react with diethylaluminum cyanide leading to anti-β-dibenzylamino-α-hydroxycyanides as the major diastereoisomers in good yields and diastereomeric excesses. Hydrolysis of the nitrile derivatives allows the synthesis of enantiopure β-amino-α-hydroxy acids.