201608-24-4

Upstream product

• 64-17-5 ethanol 
• 201230-82-2 carbon monoxide 
• 201608-21-1 Trifluoro-methanesulfonic acid 4-((2R,4S)-3-benzoyl-2-tert-butyl-1,4-dimethyl-5-oxo-imidazolidin-4-yl)-phenyl ester 
• 98-88-4 benzoyl chloride 
• 201608-20-0 (2R,5S)-1-Benzoyl-5-(4-benzyloxyphenyl)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one 
• 201608-19-7 (2R,5R)-1-Benzoyl-5-(4-benzyloxyphenyl)-2-tert-butyl-3-methylimidazolidin-4-one 
• 180715-66-6 (R)-4-Benzyloxyphenyl-N-methylglycinamide 
• 630-19-3 pivalaldehyde 
• 71336-83-9 Methyl-D-p-benzyloxyphenylglycinat 
• 69489-40-3 D-2-[p-(benzyloxy)phenyl]glycine 
• 22818-40-2 D-4-hydroxyphenylglycine 

Relevant academic research and scientific papers

Stereoselective synthesis of (S)-MPPG, (S)-MTPG and (S)-(+)-αM4CPG from (R)-4-hydroxyphenylglycine

(R)-4-Hydroxyphenylgrycine was protected with a benzyl group and a methyl group was introduced at the α position by using the self-regeneration-of-stereocentre method. After the 4-hydroxy group had been converted into the corresponding trifluoromethanesulfonate (triflate), three palladium-catalyzed reactions were employed to furnish (S)-α-methyl-4-phosphonophenylglycine [(S)-MPPG], (S)-α-methyl-4-(tetrazol-5-yl)phenylglycine [(S)-MTPG] and (S)-4-carboxyphenyl-α-methylglycine [(S)-αM4CPG], a class of new and selective antagonists of metabotropic glutamate receptors.

Stereoselective synthesis of (S)-(+)-αM4CPG, a selective antagonist of metabotropic glutamate receptors

The synthesis, from (R)-4-hydroxyphenylglycine, of (+)-α-methyl-4- carboxy-phenylglycine ((+)-αM4CPG), a new and selective antagonist of metabotropic glutamate receptor, and assignment of its absolute configuration, are described.