33551-74-5

Upstream product

• 14380-85-9 (S)-methyl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate 
• 132785-20-7 (2R,3R)-3-bromo-N-phthaloylphenylalanine methyl ester 
• 196092-86-1 (R)-3-Bromo-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionic acid methyl ester 

Relevant academic research and scientific papers

SYNTHESIS OF HOMOCHIRAL HYDROXY-α-AMINO ACID DERIVATIVES

Treatment of N-phthaloyl-α-amino acid methyl esters with N-bromosuccinimide, followed by reaction with silver nitrate in aqueous acetone, affords homochiral hydroxy-α-amino acid derivatives, the stereochemistry of which is predetermined by that of the starting amino acids.

Stereocontrolled synthesis of β-hydroxyphenylalanine and β- hydroxytyrosine derivatives

Side-chain bromination of N-phthaloyl-(S)-phenylalanine and tyrosine derivatives, followed by treatment of the product bromides with silver nitrate in aqueous acetone, affords the corresponding (2S,3R)-β-hydroxy-α- amino acids, enantiospecifically and diastereoselectively. The diastereoselectivity depends on the carboxyl protecting group. tert-Butyl esters display greater stereoselectivity than the corresponding methyl esters, presumably as a result of a steric effect, while N-tert-butylamides react diastereospecifically due to a combination of steric and electronic effects.