186586-65-2

Upstream product

• 5162-44-7 1-bromo-4-butene 
• 22263-68-9 ethyl 2-<<1(S)-phenylethyl>amino>acetate 
• 105-36-2 ethyl bromoacetate 
• 114963-47-2 N-(3-butenyl)-N-[(S)-1-phenylethyl]amine 
• 2627-86-3 (S)-1-phenyl-ethylamine 

Downstream Products

• 193538-84-0 (2S,3R)-3-methylsulfanylmethyl-1-(1-phenylethyl)-pyrrolidine-2-carboxylic acid ethyl ester 
• 867326-39-4 (2S,3R)-3-but-3-enyl-1-((S)-1-phenyl-ethyl)pyrrolidine-2-carboxylic acid ethyl ester 
• 867326-41-8 C₁₈H₂₅NO₃ 
• 867326-43-0 (2S,3R)-3-(3-phenethylamino-propyl)-1-((S)-1-phenyl-ethyl)pyrrolidine-2-carboxylic acid ethyl ester 
• 867326-45-2 (3aS,5aR)-6-phenethyl-1-((S)-1-phenylethyl)octahydropyrrolo[2,3-c]pyridin-7-one 
• 867326-47-4 (3aR,8aS)-7-phenethyl-1-((S)-1-phenyl-ethyl)decahydro-pyrrolo[2,3-c]azepine 
• 867326-51-0 C₂₄H₃₂N₂O₂ 
• 867326-49-6 (3aR,8aS)-7-phenethyl-decahydro-pyrrolo[2,3-c]azepine 
• 1196042-65-5 C₂₄H₃₇N₃O 
• 186586-71-0 (2S,3R)-3-Methyl-pyrrolidine-2-carboxylic acid ethyl ester 
• 186586-70-9 (2S,3R)-3-Methyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

Development of a Zinc-Mediated Approach to a 2,3- cis-Pyrrolidine Arginase Inhibitor

This manuscript outlines the development activities toward a robust synthesis of cis-2,3-pyrrolidine via tandem zinc-enolate cyclization/Negishi coupling that proceeds with high diastereoselectivity. The methodology facilitated a gram-scale delivery of the target API and eliminated the need for costly chiral resolutions and inefficient protecting group manipulations. A series of DFT experiments provided a transition-state model that agrees closely with the experimental observations and provides a more in-depth understanding of the observed selectivity.

Immunomodulation by IAP inhibitors

The present invention is directed to immune adjuvants containing IAP inhibitors, including Smac mimetics. The invention further provides pharmaceutical compositions and vaccines containing an IAP inhibitor and an antigen. Methods of enhancing an immune re

NOL3 IS A PREDICTOR OF PATIENT OUTCOME

The present invention features a method for determining the prognosis for survival of a cancer patient. Methods for measuring the level of NOL3 expression in a cancer cell-containing sample from a patient, and comparing the level of NOL3 expression in the

Organic compounds

Novel compounds that inhibit the binding of the Smac protein to Inhibitor of Apoptosis Proteins (IAPs) of the formula I

Asymmetric synthesis of (2S,3S)- and (2S,3R)-3-prolinomethionines: 3-Methylsulfanylmethyl-pyrrolidine-2-carboxylic acids

The synthesis of 3-prolinomethionine can be easily achieved in a diastereoselective and enantioselective way via zinc-enolate cyclisation. After transmetallation by CuCN.2LiCl, the zinc-copper derivative was reached with S-methyl methanesulfonothioate leading in a 'one-pot' procedure, to N-(α-methylbenzyl)-3-prolinomethinine benzyl ester. The α-methylbenzyl group was transformed in vinyl-oxycarbonyl and tertiobutyl-oxycarbonyl groups successively. Reprotonation of cis Voc prolinomethionine enolate at low temperature yielded the enantiomerically pure trans diastereoisomer.

New strategy for the synthesis of 3-substituted prolines

Ring formation involving a 5-exo trig cyclization between a zinc enolate and a non activated double bond led to cis diastereoisomer of 3-substituted prolines. This cyclization was achieved with transfer of chirality onto the C-2 carbon when nitrogen was protected by an α-methylbenzyl group. Reprotonation of the lithium enolate of cis derivative yielded the trans diastereoisomer.