123457-52-3

Upstream product

• 501-53-1 benzyl chloroformate 
• 108963-96-8 (S)-1-tert-butoxycarbonyl-5-methoxycarbonyl-pyrrolidin-2-one 
• 4931-66-2 methyl (S)-pyroglutamate 
• 195964-65-9 (2S)-5-allyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 
• 98-79-3 L-Pyroglutamic acid 
• 210345-08-7 (5R,2S)-5-allyl-pyrrolidine-2-carboxylic acid methyl ester 

Downstream Products

• 1096663-75-0 (2S,5R)-5-((E)-4-oxopent-2-enyl)pyrrolidine-1,2-dicarboxylic acid 1-benzylester 2-methylester 
• 1437682-49-9 benzyl (2S,2αR,5R)-(+)-2-(1-hydroxybutyl)-5-[(E)-4-oxohept-2-enyl]pyrrolidine-1-carboxylate 
• 1437682-41-1 benzyl (2S,2αR,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate 
• 1437682-39-7 benzyl (2S,2αS,5R)-(-)-5-allyl-2-(1-hydroxybutyl)pyrrolidine-1-carboxylate 
• 1437682-82-0 benzyl (2S,2αS,5R)-2-(1-hydroxyheptyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-78-4 benzyl (2S,2αS,5R)-2-(1-hydroxyheptyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-72-8 benzyl (2S,2αR,5R)-2-(1-hydroxyheptyl)-5-[(E)-4-oxohept-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-37-5 benzyl (2S,5R)-5-allyl-2-formylpyrrolidine-1-carboxylate 
• 1437682-70-6 benzyl (2S,2αS,5R)-2-(1-hydroxyheptyl)-5-[(E)-4-oxohept-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-67-1 benzyl (2S,2αR,5R)-(+)-5-allyl-2-(1-hydroxyheptyl)pyrrolidine-1-carboxylate 
• 1437682-65-9 benzyl (2S,2αS,5R)-5-allyl-2-(1-hydroxyheptyl)pyrrolidine-1-carboxylate 
• 1437682-63-7 benzyl (2S,5R)-(-)-5-allyl-2-heptanoylpyrrolidine-1-carboxylate 
• 1437682-59-1 benzyl (2S,2αR,5R)-2-(1-hydroxybutyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 
• 1437682-55-7 benzyl (2S,2αS,5R)-2-(1-hydroxybutyl)-5-[(E)-4-oxoundec-2-enyl]-pyrrolidine-1-carboxylate 

Relevant academic research and scientific papers

Synthesis and evaluation of a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane scaffold as a mimic of Xaa-trans-Pro in poly-l-proline type II helix conformation

We describe the development of a small-molecule mimic of Xaa-trans-Pro dipeptide in poly-l-proline type II helix conformation, based upon a (3R,6S,9S)-2-oxo-1-azabicyclo[4.3.0]nonane core structure. Stereoselective synthesis of the mimic from l-pyroglutamic acid is achieved in twelve linear steps and 9.9% yield. Configurational and conformational analyses are conducted using a combination of 1H NMR spectroscopy, X-ray crystallography and circular dichroism spectroscopy; and evaluation of the mimic as a promising surrogate dipeptide, in a protein-protein interaction between the SH3 domain of human Fyn kinase (Fyn SH3) and peptidomimetics of its biological ligand, are conducted by 1H-15N HSQC NMR titration experiments.

Olefin metathesis based approach to diversely functionalized pyrrolizidines and indolizidines; total synthesis of (+)-monomorine

New scaffolds for the stereoselective synthesis of diversely functionalized chiral enantiopure indolizidines and pyrrolidines were synthesized from the cross and ring-closing metathesis reactions of appropriate intermediates, readily available from L-pyroglutamic acid. The versatility of this strategy was demonstrated by the synthesis of an indolizidine-based azasugar analogue and of the natural alkaloid (+)-monomorine.