153080-85-4

Upstream product

• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 100-39-0 benzyl bromide 

Downstream Products

• 750638-93-8 (2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 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 
• 464173-86-2 (4R,5S)-N^α-tert-butoxycarbonyl-5-allyl-4-benzyl-L-proline ethyl ester 
• 464173-87-3 (4R,5S)-N^α-tert-butoxycarbonyl-4-benzyl-5-(2-oxoethyl)-L-proline ethyl ester 
• 464173-85-1 (4R)-N^α-tert-butoxycarbonyl-4-benzyl-5-methoxy-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 

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.

New enantioselective approach to α-allokainoids by Michael addition to chiral 4-substituted 2,3-didehydroprolinate

(-) and (+) α-Allokainoids hydrochlorides 3 and 4 were obtained by hydrolysis of the corresponding Michael adducts resulting from the addition of diethyl malonate to chiral N-urethane protected ethyl 4-benzyl-2,3-didehydroprolinates 9 and 13 respectively.

Stereoselective Reactions of Lithium Enolates Derived from N-BOC Protected Pyroglutamic Esters

The lithium enolates of N-Boc protected pyroglutamic ethyl or tert-butyl esters react with electrophiles in good yield without epimerization of the chiral centre.With benzyl bromides the process is stereospecific, yielding exclusively the trans isomer.However, with other reactive electrophiles a 2:1 tans/cis diastereometric mixture was obtained, regardless of the steric bulk of the ester group.