129866-73-5

Basic information

• Product Name: (2S,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester
• Synonyms: (2S,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester
• CAS NO: 129866-73-5
• Molecular Weight: 393.362
• Mol File: 129866-73-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester(129866-73-5)
• EPA Substance Registry System: (2S,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester(129866-73-5)

Safety Data

• Hazardous Substances Data: 129866-73-5(Hazardous Substances Data)

Upstream product

• 121-39-1 ethyl 3-phenylglycidate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 1002753-12-9 (2S,3S)-3-Azido-2-hydroxy-3-phenyl-propionic acid 
• 129866-71-3 Methyl (2S,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 99458-15-8 Methyl (2R,3S)-(+)-2-hydroxy-3-azido-3-phenyl-propionate 
• 127053-44-5 Methyl (2R,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate 
• 100-52-7 benzaldehyde 
• 54885-10-8 sodium (E)-3-phenylglycidate 
• 25957-39-5 Sodium Z-3-phenyl oxirane-2-carboxylate 
• 119628-74-9 trans-(4S^*,5R^*)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 121-39-1 ethyl cis-3-phenylglycidate 
• 20445-31-2 MTPA 
• 127053-48-9 Methyl (2R^*,3R^*)-3-phenyl-1H-aziridine-2-carboxylate 
• 129939-42-0 Sodium (+)-(2S,3R)-E-3-phenyl oxirane-2-carboxylate 

Relevant articles and documents

Synthesis of all four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate

Sodium -E3-phenylglycidate (±)-2E was prepared using the Darzens' procedure. Classical resolution with 1-phenylethylamine afforded optically pure salts (+)-(2S,3R)-2E and (-)-(2R,3S)-2E. Alternatively, (±)-2E was converted into (±)-2Z by ring opening of ethyl ester (±)1E with hydrogen bromide, followed by recyclization and saponification. Classical resolution of (±)-2Z with ephedrine afforded optically pure salts (+)-(2S,3S)-2Z and (-)-(2R,3R)-2Z Treatment of the four sodium salts with sodium azide followed by esterification gave hydroxy azido esters 3, which were finally converted into the four homochiral stereoisomers of methyl 3-phenyl-1H-aziridine-2-carboxylate 5 in a reaction with triphenylphosphine and subsequent heating of the initially formed oxazaphospholidines 4.