201608-25-5

Basic information

• Product Name: (S)-MPPG
• Synonyms: ALPHA-METHYL-4-PHOSPHONOPHENYLGLYCINE;BENZENEACETIC ACID, A-AMINO-A-METHYL-4-PHOSPHONO-,(AS)-;(S)-MPPG;(S)-MPPG (CYCLIC);(S)-A-METHYL-4-PHOSPHONOPHENYLGLYCINE;(S)-ALPHA-METHYL-4-PHOSPHONOPHENYLGLYCINE;(S)-1-AMINO-5-PHOSPHONOINDANE-1-CARBOXYLIC ACID;(S)-MPPG(alpha-METHYL-4-PHOSPHONOPHENYLGLYCINE)
• CAS NO: 201608-25-5
• Molecular Formula: C9H12NO5P
• Molecular Weight: 245.17
• Mol File: 201608-25-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-MPPG(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-MPPG(201608-25-5)
• EPA Substance Registry System: (S)-MPPG(201608-25-5)

Safety Data

• Hazardous Substances Data: 201608-25-5(Hazardous Substances Data)

Usage

Uses

(S)-MPPG is a highly potent L-AP4-sensitive receptor antagonist.

Upstream product

• 201608-22-2 [4-((2R,4S)-3-Benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl]-phosphonic acid diethyl ester 
• 220024-56-6 N-[(R)-(2-hydroxy-1-phenylethyl)]-(S)-2-amino-2-methyl-(4'-diethylphosphonophenyl)acetic acid methyl ester 
• 220024-55-5 (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-[4-(diethoxy-phosphoryl)-phenyl]-propionic acid methyl ester 
• 220024-53-3 (S)-2-[Benzyloxycarbonyl-((R)-2-hydroxy-1-phenyl-ethyl)-amino]-2-(4-bromo-phenyl)-propionic acid methyl ester 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 69489-40-3 D-2-[p-(benzyloxy)phenyl]glycine 
• 71336-83-9 Methyl-D-p-benzyloxyphenylglycinat 
• 180715-66-6 (R)-4-Benzyloxyphenyl-N-methylglycinamide 
• 201608-19-7 (2R,5R)-1-Benzoyl-5-(4-benzyloxyphenyl)-2-tert-butyl-3-methylimidazolidin-4-one 
• 201608-20-0 (2R,5S)-1-Benzoyl-5-(4-benzyloxyphenyl)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one 
• 201608-21-1 Trifluoro-methanesulfonic acid 4-((2R,4S)-3-benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl 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.