464173-85-1

Upstream product

• 67-56-1 methanol 
• 750638-93-8 (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 153080-85-4 ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 

Downstream Products

• 166941-69-1 Ethyl (2S,4R,5R)-4-benzyl-5-butylprolinate 
• 464174-02-5 (4R,5S)-N^α-tert-butoxycarbonyl-5-[(3R)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester 
• 464173-89-5 (4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester 
• 464173-87-3 (4R,5S)-N^α-tert-butoxycarbonyl-4-benzyl-5-(2-oxoethyl)-L-proline ethyl ester 
• 464173-88-4 (4R,5S)-N^α-tert-butoxycarbonyl-5-[3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)allyl]-4-benzyl-L-proline ethyl ester 
• 550375-63-8 (6S,8R)-8-Benzyl-1-chloro-4-oxo-3-(3-trifluoromethyl-benzylamino)-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic acid ethyl ester 
• 550375-56-9 (6S,8R)-8-Benzyl-1,3-dichloro-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrazine-6-carboxylic acid ethyl ester 
• 464173-86-2 (4R,5S)-N^α-tert-butoxycarbonyl-5-allyl-4-benzyl-L-proline ethyl ester 

Relevant academic research and scientific papers

Design and synthesis of potent, non-peptide inhibitors of HCV NS3 protease

Starting from a hexapeptide boronic acid lead, 3-amino bicyclic pyrazinones as novel β-sheet dipeptide mimetics have been designed and synthesized. Side-chain manipulation of this scaffold generated a series of potent, nonpeptidic inhibitors of HCV NS3 protease.

Stereoselective synthesis of dipeptide β-turn mimetics: 7-Benzyl and 8-phenyl substituted azabicyclo[4.3.0]nonane amino acid esters

A stereoselective method has been developed for the synthesis of 7- and 8-substituted dipeptide β-turn mimetic azabicyclo[4.3.0]nonane amino acid esters. The allyl groups were introduced in high diastereoselectivity, controlled by 3-phenyl or 4-benzyl groups in pyroglutamic acid derivatives 3 or 9, respectively. The precursors, dehydroamino acids 7 and 13 derived from 5 or 11, underwent asymmetric hydrogenations with Burk's DuPHOS Rh(I)-based catalysts to furnish α-amino acid derivatives in high stereoselectivity. The resulting amino acids 8 and 14 were converted to the β-turn mimetics 6,5-bicyclic lactams 1a-d in high yields.

Stereoselective Addition of Grignard-Derived Organocopper Reagents to N-Acyliminium Ions: Synthesis of Enantiopure 5- and 4,5-Substituted Prolinates

Alkylation of nonracemic N-acyliminium ions derived from proline and 4-substituted prolines has been extended to different types of Grignard-derived organocopper reagents.The reaction proceeds with high yield and stereoselectivity to yield 5-mono- and 4,5-disubstituted prolinates.The stereochemistry is controlled by the formation of a RCu-? complex intermediate between the N-acyliminium ion, the carbonyl group of the ester, and the copper species.