461639-00-9

Upstream product

• 531539-21-6 (2S)-5-oxo-pyrrolidine-2-carboxylic acid 3-methyl-oxetan-3-ylmethyl ester 
• 98-79-3 L-Pyroglutamic acid 
• 501-53-1 benzyl chloroformate 
• 3143-02-0 3-hydroxymethyl-3-methyloxethane 
• 531539-18-1 (2S)-1-benzyloxycarbonyl-5-oxo-pyrrolidine-2-carboxylic acid 2-(3-methyl-oxetan-3-yl-methyl) ester 

Downstream Products

• 531539-23-8 (2S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 531539-31-8 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(1-naphthyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-29-4 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-(4-chlorophenyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-43-2 (2S,3R,4S)-3-methyl-2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-5-oxo-4-phenylselenenyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-26-1 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-n-butyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-28-3 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-phenyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-36-3 (2S,3R)-1-(benzyloxycarbonyl)-3-(4-chlorophenyl)-glutamic acid 
• 531539-25-0 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-ethyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-35-2 (2S,3R)-1-(benzyloxycarbonyl)-3-phenyl-glutamic acid 
• 531539-34-1 (2S,3S)-1-(benzyloxycarbonyl)-3-n-butyl-glutamic acid 
• 531539-44-3 (2S)-3-methyl-2-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester 
• 531539-24-9 (2S,3S)-2-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-5-oxo-3-methyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 531539-33-0 (2S,3S)-1-(benzyloxycarbonyl)-3-ethyl-glutamic acid 
• 531539-32-9 (2S,3S)-1-(benzyloxycarbonyl)-3-methyl-glutamic acid 

Relevant academic research and scientific papers

A stereoselective synthesis of 3-substituted (S)-pyroglutamic and glutamic acids via OBO ester derivatives

(S)-Pyroglutamic acid is transformed to the Cbz-protected 4-methyl-2,6,7-trioxabicyclo[2.2.2] octane (OBO) ester. This ortho ester functionality is employed as a bulky steering group for stereoselective introduction of alkyl and aryl groups via 1,4-cuprate addition to 3,4-unsaturated pyroglutamates. After deprotection and ringopening, 3-substituted glutamic acids are obtained.