62023-60-3

Usage

Uses

Used in Medicinal Chemistry:
(2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid is used as a key intermediate in the synthesis of peptide-based drugs, leveraging its unique stereochemistry and functional groups to create novel therapeutic agents.
Used in Drug Discovery:
As a building block in drug discovery, (2R,3S)-N-(benzyloxycarbonyl)-3-amino-2-hydroxy-4-phenylbutanoic acid is utilized to develop new chemical entities with potential therapeutic applications, capitalizing on its structural features to enhance the properties of resulting compounds.

Upstream product

• 151-50-8 potassium cyanide 
• 501-53-1 benzyl chloroformate 
• 62023-57-8 (S)-1-(2'-benzyloxycarbonylamino-3'-phenylpropanoyl)-3,5-dimethylpyrazole 
• 126015-22-3 (2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 59830-60-3 benzyl (1S)-(1-formyl-2-phenylethyl)carbamate 
• 172696-23-0 (2S,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester 
• 172696-22-9 (2R,3S)-N-(benzyloxycarbonyl)-AHAP-(3-amino-2-hydroxy-4-phenylbutanoic acid) ethyl ester 
• 126015-21-2 [(1S,2R)-1-Benzyl-2-cyano-2-((1S,3S)-3-hydroxy-1-methyl-butoxy)-ethyl]-carbamic acid benzyl ester 
• 126061-52-7 [(1S,2R)-1-Benzyl-2-cyano-2-((1R,3R)-3-hydroxy-1-methyl-butoxy)-ethyl]-carbamic acid benzyl ester 
• 113283-75-3 [(S)-1-((4S,6S)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 113283-78-6 [(S)-1-((4R,6R)-4,6-Dimethyl-[1,3]dioxan-2-yl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 114744-85-3 [(S)-1-(methoxy-methyl-carbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 121253-57-4 β-<<(phenylmethoxy)carbonyl>amino>-α-oxobenzenebutanoic acid ethyl ester 
• 121253-53-0 2-ethoxy-5-phenyl-4-<<(phenylmethoxy)carbonyl>amino>-3-oxo-1-pentene 

Downstream Products

• 191849-91-9 1-<(2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutyryl>-N-tert-butyl-L-prolinamide 
• 141171-72-4 (2S,3S)-3-(N-benzyloxycarbonyl)amino-2-hydroxy-4-phenylbutyryl-L-prolyl-tert-butyl amide 
• 863640-18-0 (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoyl-(S)-proline methyl ester 
• 62023-63-6 (2R,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid 

Relevant academic research and scientific papers

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

Selectivity in the inhibition of HIV and FIV protease: Inhibitory and mechanistic studies of pyrrolidine-containing α-keto amide and hydroxyethylamine core structures

This paper describes the development of new pyrrolidine-containing α-keto amide and hydroxyethylamine core structures as mechanism based inhibitors of the HIV and FIV proteases. It was found that the α-keto amide core structure 2 is approximately 300-fold better than the corresponding hydroxyethylamine isosteric structure and 1300-fold better than the corresponding phosphinic acid derivative as an inhibitor of the HIV protease. The α-keto amide is however not hydrated until it is bound to the HIV protease as indicated by the NMR study and the X-ray structural analysis. Further analysis of the inhibition activities of hydroxyethylamine isosteres containing modified pyrrolidine derivatives revealed that a cis-methoxy group at C-4 of the pyrrolidine would improve the binding 5- and 25-fold for the trans-isomer. When this strategy was applied to the α-keto amide isostere, a cis-benzyl ether at C-4 was found to enhance binding 3-fold. Of the core structures prepared as inhibitors of the HIV protease, none show significant inhibitory activity against the mechanistically identical FIV protease, and additional complementary groups are needed to improve inhibition.

Diastereoselective process for the preparation of intermediates useful for the synthesis of peptide derivatives

A diastereoselective process for the preparation of compounds of formula STR1 (wherein R and R1 have the meanings reported in the specification and the asterisks show the asymmetric carbon atoms) starting from the corresponding N-protected 2-am

Tributyltin Cyanide, a Novel Reagent for the Stereoselective Preparation of 3-Amino-2-hydroxy Acids via Cyanohydrin Intermediates

Reaction of tributyltin cyanide with optically active 2-N-benzyloxycarbonylamino aldehydes 1 gives the corresponding O-tributylstannyl cyanohydrins 2 and 3 stereoselectively.Compounds 2 and 3 are transformed in situ into the methyl 3-N-benzyloxycarbonylam

Stereoselection in the Synthesis of threo- and erythro-3-Amino-2-hydroxy-4-phenyl-butanoic Acid using Chiral Acetal Templates

Boron trifluoride-diethyl ether mediated addition of trimethylsilylcyanide (TMSCN) to the chiral acetals derived from Z-L- and Z-D-phenyl alaninal, Z-N-benzyloxycarbonyl), and (+)-(2S,4S)- and (-)-(2R,4R)-2,4-pentanediol stereoselectivity gave the four st

Diastereoselective process for the preparation of intermediates useful for the synthesis of peptide derivatives

A diastereoselective process for the preparation of compounds of formula (wherein R and R1 have the meanings reported in the specification and the asterisks show the asymmetric carbon atoms) starting from the corresponding N-protected 2-amino-3