7309-53-7

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 
• 195196-19-1 C₄₁H₆₁NO₄Si₂ 
• 100-52-7 benzaldehyde 
• 127001-34-7 N-Benzylidene<(R)-(-)-α-methylbenzyl>amine N-oxide 
• 55325-49-0 (±)-anti-3-amino-2-hydroxy-3-phenylpropanamide 
• 1566-68-3 (2RS,3SR)-2,3-epoxy-3-phenyl-propionic acid 
• 195196-15-7 (3S,4S)-4-hydroxy-3-phenyl-N-(1-phenylethyl)isoxazolidinone 

Downstream Products

• 140408-37-3 ethyl (2R^*,3R^*)-3-phenyl-3-amino-2-hydroxypropanoate hydrochloride 
• 100-52-7 benzaldehyde 
• 2835-06-5 phenylglycin 
• 144541-45-7 methyl (2S,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 7309-55-9 (2S,3S)-N-benzoyl-3-phenylisoserine 

Relevant academic research and scientific papers

Synthesis method of alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer

The invention relates to a synthesis method of an alpha-hydroxyl-beta-amino acid simplex stereoscopic isomer. The method mainly solves the technical problems that an existing synthesis method uses expensive chiral ligand or highly-toxic raw materials and is not suitable for industrial production. The method includes the steps of firstly, synthesizing substitutive alpha-hydroxyl-beta-amino acid despinner according to a literature method; secondly, stereoscopically and selectively synthesizing an alpha-hydroxyl-beta-amino acid simplex isomer of an (S,S) structure and an alpha-hydroxyl-beta-aminoacid simplex isomer of an (R,R) structure with penicillin G acylase. The method is suitable for preparing the alpha-hydroxyl-beta-amino acid simplex isomers efficiently at low cost.

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.

Totally stereocontrolled nitrone-ketene acetal based synthesis of (2S,3S)-N-benzoyl-and N-boc-phenylisoserine

A novel, nitrone-ketene acetal based approach to enantiopure (2S,3S)-N- benzoyl- and N-boc-phenylisoserine has been realized. The convergent approach, which involves the intermediacy of isoxazolidinones, proceeds in up to 59% overall yield and requires only three operations from the starting nitrones.