157683-55-1

Upstream product

• 67-56-1 methanol 
• 214122-05-1 (4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile 
• 1161-13-3 N-Cbz-L-Phe 
• 25613-60-9 Nα-carbobenzyloxy-L-phenylalanine N-carboxanhydride 
• 1047404-15-8 (S)-3-Benzyloxycarbonylamino-2-hydroxy-4-phenyl-butyric acid methyl ester 

Downstream Products

• 181047-31-4 (S)-3-Benzyloxycarbonylamino-2,2-difluoro-4-phenyl-butyric acid methyl ester 
• 126015-23-4 (2S,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 126015-22-3 (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 322729-62-4 (3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 322729-68-0 (3S)-2-oxo-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 322729-60-2 (2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 
• 322729-66-8 (2R,3S)-2-hydroxy-4-phenyl-3-[[[3-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of cyanoketophosphoranes, precursors of β-amino-α-keto- esters from uncas

Cyanomethylene triphenylphosphoranes of N-protected amino acids were synthesized from the corresponding N-urethane protected or amino acid N- carboxyanhydrides (UNCAs) by reaction with cyanomethyltriphenylphosphonium chloride in good yields. These compoun

Azobenzene-containing, peptidyl α-ketoesters as photobiological switches of α-chymotrypsin

Three photoswitchable, peptidomimetic inhibitors of α-chymotrypsin have been synthesised. The compounds comprise an azobenzene, an α-ketoester and L-phenylalanine. The compounds were photoisomerised to give enriched states of the (E) and (Z) isomers and t

Inactivation of serine protease, α-chymotrypsin by fluorinated phenylalanine analogues

Fluorinated phenylalanine analogues were found to be slow-binding or reversible competitive inhibitors of α-chymotrypsin. A series of these compounds were designed to inactivate α-chymotrypsin as a result of the formation of hydrogen-bonding between fluorine atom of the inhibitors and the amide protons known as oxy-anion hole in the active-site of serine and cysteine proteases.

(Cyanomethylene)phosphoranes as Novel Carbonyl 1,1-Dipole Synthons: An Efficient Synthesis of α-Keto Acids, Esters, and Amides

Carboxylic acids react with (cyanomethylene)triphenylphosphorane in the presence of EDCI to form cyano keto phosphoranes.The resulting ylides may then be oxidatively cleaved with ozone to form α,β-diketonitriles.These highly electrophilic products may then be converted in situ to α-keto acids, esters, and amides.

First Synthesis of Enantiomerically Pure N-Protected β-Amino-α-Keto Esters from α-Amino Acids and Dipeptides

A racemization-free route from N-protected α-amino acids and dipeptides to N-protected β-amino-α-keto esters is described, involving the sequence: diazoketone formation, Wolff rearrangement in methanol, diazo transfer, and oxidation with dimethyldioxirane.