161022-75-9

Upstream product

• 60398-42-7 methyl (3S)-3-{[(tert-butoxy)carbonyl]amino}-4-phenylbutanoate 
• 161022-73-7 (2S,3R,4S)-2-((S)-1-tert-Butoxycarbonylamino-2-phenyl-ethyl)-4-dibenzylamino-3-hydroxy-5-phenyl-pentanoic acid methyl 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.