1002753-12-9

Basic information

• Product Name: (2S,3S)-3-Azido-2-hydroxy-3-phenyl-propionic acid
• CAS NO: 1002753-12-9
• Molecular Weight: 207.189
• Mol File: 1002753-12-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-3-Azido-2-hydroxy-3-phenyl-propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-3-Azido-2-hydroxy-3-phenyl-propionic acid(1002753-12-9)
• EPA Substance Registry System: (2S,3S)-3-Azido-2-hydroxy-3-phenyl-propionic acid(1002753-12-9)

Safety Data

• Hazardous Substances Data: 1002753-12-9(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 121-39-1 ethyl 3-phenylglycidate 
• 129939-42-0 Sodium (+)-(2S,3R)-E-3-phenyl oxirane-2-carboxylate 

Downstream Products

• 119628-74-9 cis-(4S,5S)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 
• 129866-73-5 (2R,3S)-3-Phenyl-1-(3,3,3-trifluoro-2-methoxy-2-phenyl-propionyl)-aziridine-2-carboxylic acid methyl ester 
• 129939-52-2 Methyl (2R,3S)-3-phenyl-1H-aziridine-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.