118545-53-2

Upstream product

• 34582-33-7 α-tert-butyl-γ-methyl L-Glu diester hydrochloride 
• 3077-51-8 γ-methyl L-glutamate hydrochloride 
• 56-86-0 L-glutamic acid 
• 79640-72-5 L-glutamic acid 1-tert-butyl ester 5-methyl ester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 118545-50-9 α-tert-butyl γ-methyl N-trityl-L-glutamate 
• 67-64-1 acetone 
• 76-83-5 trityl chloride 

Downstream Products

• 125089-98-7 t-butyl 2-tritylamino-4-carboxy-5-hydroxy-5-methyl-(2S)-hexanoate 

Relevant academic research and scientific papers

SYNTHESIS OF NONPROTEINOGENIC AMINO ACIDS PART 2: PREPARATION OF A SYNTHETIC EQUIVALENT OF THE γ-ANION SYNTHON FOR ASYMMETRIC AMINO ACID SYNTHESIS

The synthesis of α-t-butyl γ-methyl N-trityl-(S)-glutamate (12) from (S)-glutamic acid (6) is described.Diester (12), on treatment with lithium isopropylcyclohexylamide followed by the addition of carbonyl compounds, reacts to give the γ-substituted glutamic acid derivatives (13a-i) with retention of optical purity at the α centre.

Stereospecific Amino Acid Synthesis; Preparation of the γ-Anion derived from Glutamic Acid

Reaction of α-t-butyl γ-methyl N-trityl-L-glutamate (7) with lithium isopropylcyclohexylamide in hexane leads to the specific formation of the γ-ester enolate, a potential synthetic equivalent to the γ-anion synthon for stereospecific α-amino acid synthesis.