159516-91-3

Upstream product

• 56-86-0 L-glutamic acid 
• 152500-30-6 (S)-5-Benzyloxymethyl-3-[1-hydroxy-meth-(E)-ylidene]-2-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 100-39-0 benzyl bromide 
• 152500-34-0 (3R,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethyl-2-pyrrolidinone 
• 152500-33-9 (3S,5S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-methoxymethyl-2-pyrrolidinone 
• 152500-29-3 (S)-5-benzyloxymethyl-1-tert-butoxycarbonyl-3-N,N-dimethylaminomethylidene-2-pyrrolidinone 
• 152500-27-1 (S)-5-benzyloxymetyl-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 152500-20-4 (S)-5-ethoxycarbonyl-1-(4-methoxybenzyl)-2-pyrrolidinone 
• 152500-21-5 (S)-5-benzyloxymetyl-1-tert-butoxycarbonyl-2-pyrrolidinone 
• 152500-25-9 (S)-N-(4-methoxybenzyl)glutamic acid 
• 130603-28-0 (S)-5-benzyloxymetyl-2-pyrrolidinone 
• 152500-26-0 (S)-5-(hydroxymethyl)-1-(4-methoxyphenylmethyl)-2-pyrrolidinone 
• 24424-99-5 di-tert-butyl dicarbonate 
• 152500-37-3 (2S,3R,5S)-5-benzyloxymethyl-2-cyano-1-tert-butoxycarbonyl-3-methoxymethylpyrrolidine 

Downstream Products

• 159516-92-4 (2S,3R,5S)-3-acetoxymethyl-5-benzyloxymethyl-1-tert-butoxycarbonyl-2-cyanopyrrolidine 

Relevant academic research and scientific papers

Synthetic studies on quinocarcin and its related compounds. 3. Synthesis of 5-substituted- and 3,5-disubstituted-2-formyl-pyrrolidine derivatives, the key D-ring fragments of enantiomeric pairs of quinocarcin and 1

The title synthesis was accomplished by employing each enantiomer of glutamic acid and pyroglutamic acid as chiral starting materials.

Enantioselective synthesis of 5-substituted and 3,5-disubstituted-2-formylpyrrolidine derivatives, the key D-ring fragments of (-)-quinocarcin and (-)-10-decarboxyquinocarcin

The title synthesis was achieved starting from (S)-glutamic acid and (S)-pyroglutamic acid by featuring formation of an N-protected aminal, substitution of the methoxy group with cyanide anion, and reduction of the cyanide to an aldehyde as common key steps.