220024-53-3

Basic information

• Product Name: (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester
• Synonyms: (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester
• CAS NO: 220024-53-3
• Molecular Weight: 512.4
• Mol File: 220024-53-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester(220024-53-3)
• EPA Substance Registry System: (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester(220024-53-3)

Safety Data

• Hazardous Substances Data: 220024-53-3(Hazardous Substances Data)

Upstream product

• 501-53-1 benzyl chloroformate 

Downstream Products

• 220024-56-6 N-[(R)-(2-hydroxy-1-phenylethyl)]-(S)-2-amino-2-methyl-(4'-diethylphosphonophenyl)acetic acid methyl ester 
• 169209-65-8 MPPG 
• 220024-55-5 (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-[4-(diethoxy-phosphoryl)-phenyl]-propionic acid methyl ester 

Relevant articles and documents

Asymmetric strecker-type reaction of α-aryl ketones. Synthesis of (S)- αM4CPG, (S)-MPPG, (S)-AIDA, and (S)-APICA, the antagonists of metabotropic glutamate receptors

Heating a mixture of α-aryl ketone with (R)-phenylglycinol produces a mixture of imine and 1,3-dioxazolidine. Treatment of this mixture with trimethylsilyl cyanide followed by transformation of nitrile to ester gives Strecker-type reaction products. The diastereoselectivity of the generated α-amino esters is from 2/1 to 7/1, and the (R,S)isomer is found as the major product. The (R,S) and (R,R)isomers can be separated by conversion to their N-Cbz or cyclization derivatives. Using this methodology, four antagonists of metabotropic glutamate receptors, (S)-αM4CPG, (S)-MPPG, (S)AIDA, and (S)- APICA, are synthesized.