129866-72-4

Basic information

• Product Name: Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate
• Synonyms: Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate
• CAS NO: 129866-72-4
• Molecular Weight: 221.216
• Mol File: 129866-72-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate(129866-72-4)
• EPA Substance Registry System: Methyl (2S,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate(129866-72-4)

Safety Data

• Hazardous Substances Data: 129866-72-4(Hazardous Substances Data)

Upstream product

• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 130608-01-4 (2S,3R)-methyl 2-acetoxy-3-azido-3-phenylpropanoate 
• 129939-43-1 Sodium (+)-(2S,3S)-Z-3-phenyl oxirane-2-carboxylate 
• 54885-10-8 sodium (E)-3-phenylglycidate 
• 121-39-1 ethyl cis-3-phenylglycidate 

Downstream Products

• 161759-90-6 (+)-(2S,3R)-methyl 3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenylpropanoate 
• 129939-53-3 Methyl (2R,3R)-3-phenyl-1H-aziridine-2-carboxylate 
• 119628-74-9 trans-(4S,5R)-2,2,2,4-Tetraphenyl-5-methoxycarbonyl-1,3,2-oxazaphospholidine 

Relevant articles and documents

Determination of the structure and its absolute configuration of 2″-hydroxynicotianamine, an inhibitor against Angiotensin-I converting enzyme in buckwheat, through the total synthesis

Nicotianamine is known as an inhibitor against Angiotensin-I Converting Enzyme (ACE). We synthesized a new nicotianamine derivative with an additional hydroxy group isolated from buckwheat (Fagopyrum esculentum Moench) powder and determined its regio and stereochemistry unambiguously by the enantioselective synthesis of diastereomers.

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.