365402-94-4

Upstream product

• 365402-91-1 E-(S_S,2S,3S)-(+)-N-p-toluenesulfinyl-2-benzyloxymethyl-2-carbomethoxy-3-phenylaziridine 
• 365402-92-2 methyl E-(2S,3S)-(-)-2-benzyloxymethyl-3-phenyl-1H-aziridine-2-carboxylate 
• 350479-90-2 (S,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 365402-93-3 (S)-(+)-2-amino-2-benzyloxymethyl-3-phenylpropionic acid methyl ester 
• 93250-97-6 (2R,4S)-methyl 4-benzyl-2-tert-butyl-3-formyloxazolidine-4-carboxylate 

Downstream Products

• 205817-28-3 methyl (S)-2-benzyl-2-(tert-butoxycarbonylamino)-3-hydroxypropanoate 
• 1015251-53-2 (S)-methyl 2-benzyl-2-(benzyloxycarbonylamino)-3-hydroxypropanoate 
• 292035-12-2 (S)-2-((tert-butoxycarbonyl)amino)-3-hydroxy-2-benzylpropionic acid 
• 205817-31-8 C₂₀H₂₉N₃O₈ 
• 205817-29-4 (S)-2-(Benzyloxyamino-methyl)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

New fast and practical method for the enantioselective synthesis of α-vinyl, α-alkyl quaternary α-amino acids

We describe a fast and practical enantioselective synthesis of (S)-N-Cbz-α-vinyl, phenylalanine, suitable for the preparation of different N-Cbz-α-vinyl aminoacids of both configurations. The new protocol exploits a Wittig reaction on highly enantiomeric enriched N-Cbz-α-formyl-α-alkyl amino esters, readily accessible from (l)-serine through a stereoselective alkylation of Seebach's oxazolidine, carried out with a significant improvement of the previously reported method. The synthetic scheme is suitable for gram scale preparation of the desired product with a 94% ee.

Aziridine mediated asymmetric synthesis of α-benzylserine and α-n-butylserine

Regioselective hydrogenolysis of enantiopure 2-benzyloxyaziridine 2-carboxylates represents a general method for the asymmetric synthesis of α-substituted serines. The aziridines are readily prepared via an aza-Darzens reaction of the enolate of methyl 3-

α-Substituted quisqualic acid analogs: New metabotropic glutamate receptor group II selective antagonists

Syntheses of both the α-methyl and benzyl analogs of quisqualic acid are described. Testing of these compounds for their activity at excitatory amino acid receptors revealed a striking change in activity in comparison to quisqualic acid. This structural modification results in the loss of quisqualate's potent agonist action at both non-NMDA ionotropic glutamate receptors as well as at group I mGluRs, while allowing these analogs to acquire antagonist properties with relative selectivity for group II metabotropic glutamate receptors.