161022-73-7

Upstream product

• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 60398-42-7 methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate 

Downstream Products

• 160998-84-5 [(S)-1-((3S,4R,5S)-5-Benzyl-4-hydroxy-2-oxo-pyrrolidin-3-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester 
• 161022-75-9 ((1S,2R,3R,4S)-1-Benzyl-4-dibenzylamino-3-hydroxy-2-hydroxymethyl-5-phenyl-pentyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Addition of dilithiated methyl-3-aminobutanoate to aldehydes proceeds with ul-1,2-induction

Syntheses of 2-substituted 1-hydroxyethylene building blocks, useful as the central moiety of HIV-1 protease inhibitors, is described. Dilithiated N-protected-3-amino-4-phenylbutanoic methyl esters are reacted with aldehydes to give predominantly aldol products with l,u configuration. The diastereomeric ratio depends on the N-protecting group and on the experimental conditions. The configurations are assigned by 1H-NMR of cyclic derivatives and are supported by X-ray structure.