161453-08-3

Basic information

• Product Name: (αR,βR)-
• Synonyms: (αR,βR)-;(aR,R)--Phenyl Isoserine Hydrochloride;(αR,βR)-β-Phenyl Isoserine Hydrochloride;(2R,3R)-3-Amino-2-hydroxy-3-phenylpropanoic acid hydrochloride
• CAS NO: 161453-08-3
• Molecular Formula: C9H12ClNO3
• Molecular Weight: 217.64948
• Product Categories: Amino Acids & Derivatives;Aromatics;Chiral Reagents
• Mol File: 161453-08-3.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (αR,βR)-(CAS DataBase Reference)
• NIST Chemistry Reference: (αR,βR)-(161453-08-3)
• EPA Substance Registry System: (αR,βR)-(161453-08-3)

Safety Data

• Hazardous Substances Data: 161453-08-3(Hazardous Substances Data)

Usage

Uses

An intermediate for the synthesis of Paclitaxel, Docetaxel and their derivatives.

Upstream product

• 132127-31-2 3-Triisopropylsilyloxy-4-phenylazetidin-2-one 
• 56816-81-0 (2R,3S)-2,3-dihydroxy-3-phenyl-propionic acid 
• 104196-23-8 (2S,3S)-2,3-epoxy-3-phenyl-1-propanol 
• 104-54-1 3-Phenylpropenol 
• 133066-59-8 cis-rac-3-acetoxy-4-phenylazetidin-2-one 
• 120419-97-8 (E)-N-benzylidene-1,1,1-trimethylsilanamine 
• 144465-78-1 1-(4-Methoxyphenyl)-3-triisopropylsilyloxy-4-phenyl-2-azetidinone 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 145987-13-9 methyl (2S,3R)-2-acetoxy-3-bromo-3-phenylpropionate 
• 158341-43-6 methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 103-26-4 Methyl cinnamate 
• 201339-41-5 isopropyl 2-tert-butyldimethylsiloxy-3-(2-hydroxyphenyl)amino-3-phenylpropionate 
• 201339-46-0 (2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(2-methoxy-phenylamino)-3-phenyl-propionic acid isopropyl ester 
• 3230-45-3 (E)-N-benzylidene-2-hydroxyaniline 

Downstream Products

• 1356606-76-2 (R)-3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-hydroxy-3-phenylpropanoic acid 
• 155396-65-9 (2R,3S)-2-benzyloxy-3-tert-butoxy-carbonylamino-3-phenylpropanoic acid 
• 143527-75-7 (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine 
• 1395491-92-5 (2R,3S)-2-benzyloxy-3-tert-butoxycarbonylamino-3-phenylpropionic acid ethyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 949023-16-9 (4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid 

Relevant articles and documents

Synthesis method of phenyl isoserine hydrochloride and intermediate thereof (by machine translation)

The invention provides a method .for synthesizing phenyl isoserine hydrochloride and an intermediate thereof, II of the compound shown in formula, in the presence of a catalyst: and the method comprises the following steps, synthesizing paclitaxel and docetaxel in the following steps: synthesizing paclitaxel and docetaxel as shown in the following reaction I as shown, in the following steps: II, synthesizing paclitaxel and docetaxel in a low price . and synthesizing the paclitaxel and docetaxel in an inexpensive manner . The invention provides cheap chiral side chain raw material, for synthesizing paclitaxel and, docetaxel as shown in the following step: [,] The present invention provides cheap chiral side. chain raw materials. (by machine translation)

The N-Hydroxymethyl Group as a Traceless Activating Group for the CAL-B-Catalysed Ring Cleavage of β-Lactams: A Type of Two-Step Cascade Reaction

An efficient enzymatic two-step cascade procedure has been devised for rapid access to diverse amino acids from N-hydroxymethyl-β-lactams; representative amino acids include the antifungal agent cispentacin, intermediates for the taxol side-chain, and assorted cathepsin inhibitors. When CAL-B-catalysed hydrolyses of racemic N-hydroxymethyl-β-lactams were performed with H2O (0.5 equiv.) in iPr2O at 60 °C, relatively quick (vs. non-activated counterparts) and enantioselective (E > 200) ring cleavage reactions took place. As the ring-opened amino acids formed, the hydroxymethyl group, as a traceless activating group, underwent spontaneous in situ degradation. Consequently, the desired β-amino acid and unreacted N-hydroxymethyl-β-lactam enantiomers (ee > 95 %) were formed. The formation of polymers, induced by liberation of formaldehyde, was successfully restricted by the addition of benzylamine as a capture agent, to the enzymatic reactions. An efficient enzymatic two-step cascade procedure was devised for CAL-B-catalysed hydrolysis of racemic N-hydroxymethyl-β-lactams. Conditions in which the hydroxymethyl group serves as a traceless activating group (E > 200), giving desired β-amino acid along with unreacted starting lactam enantiomers (ee > 95 %) were identified; polymerization was controlled by addition benzylamine addition.

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.