464173-86-2

Upstream product

• 464173-85-1 (4R)-N^α-tert-butoxycarbonyl-4-benzyl-5-methoxy-L-proline ethyl ester 
• 762-72-1 allyl-trimethyl-silane 
• 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 

Downstream Products

• 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 
• 464173-88-4 (4R,5S)-N^α-tert-butoxycarbonyl-5-[3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)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 

Relevant academic research and scientific papers

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.