141901-21-5

Basic information

• Product Name: (2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide
• Synonyms: (2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide
• CAS NO: 141901-21-5
• Molecular Weight: 180.206
• Mol File: 141901-21-5.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: (2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide(141901-21-5)
• EPA Substance Registry System: (2R,3S) 2-hydroxy-3-amino-3-phenylpropionamide(141901-21-5)

Safety Data

• Hazardous Substances Data: 141901-21-5(Hazardous Substances Data)

Upstream product

• 19190-80-8 cis-methyl 2,3-epoxy-3-phenylpropanoate 
• 121-39-1 ethyl cis-3-phenylglycidate 
• 99528-65-1 (2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 19190-80-8 methyl trans-3-phenylglycidate 

Downstream Products

• 136561-53-0 (2R,3S)-2-hydroxy-3-amino-3-phenylpropionic acid 
• 33069-62-4 taxol 
• 6049-55-4 (±)-anti-3-amino-2-hydroxy-3-phenylpropanoic acid 
• 132201-33-3 (2R,3S)-N-benzoyl-3-phenylisoserine 
• 32981-85-4 syn-(+/-)-2-hydroxy-3-(benzoylamino)-3-phenylpropanoic acid methyl ester 
• 32981-85-4 methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate 
• 7309-55-9 N-benzoyl-(2R^*,3S^*)-3-phenylisoserine 
• 130517-90-7 Butyric acid (1R,2R)-2-butyrylamino-1-carbamoyl-2-phenyl-ethyl ester 

Relevant articles and documents

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 practical and stereoselective synthesis of taxol side chain

Apractical and efficient synthesis of taxol C-13 side chain from cheap and easily available starting material is described.

Stereospecific preparation of glycidic esters from 2-chloro-3-hydroxyesters. Application to the synthesis of (2R,3R)-3-phenylisoserine

Cis- and trans-glycidic esters may be synthesized in high enantiomeric purities by cyclisation with potassium carbonate in DMF of the corresponding syn- or anti-2-chloro-3-hydroxyesters, prepared by microbial reduction of 2-chloro-3-oxoesters. In contrast, more basic media such as sodium ethylate afford exclusively the trans-isomer, whatever the stereochemistry of the starting 2-chloro-3-hydroxyester is. Cyclisation of deuterated compounds showed that this result was due to a rapid isomerisation of the syn esters into anti isomers before cyclisation. An application of this reaction to the synthesis of (2R,3R)-3-phenylisoserine is described.