488760-74-3

Upstream product

• 117384-45-9 (4R,5R)-di-tert-butyl tartrate 
• 7633-32-1 tert-butyl glyoxylate 
• 794525-83-0 tert-butyl (S)-3-oxo-1-phenyl-4-(phenylsulfinyl)butan-2-ylcarbamate 
• 176504-90-8 dimethyl [(3S)-4-phenyl-3-[N-(tert-butyloxycarbonyl)amino]-2-oxobutyl]phosphonate 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 488760-73-2 tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-6-phenyl-(E)-2-hexenoate 

Downstream Products

• 668436-17-7 tert-butyl (4R,5S)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-hexanoate 

Relevant academic research and scientific papers

Stereoselective synthesis of photoreactive peptidomimetic γ-secretase inhibitors

The first asymmetric synthesis of novel, potent photoreactive γ-secretase inhibitors 2 and 3 has been accomplished. Two Stereoselective methods for the preparation of lactone 9 are described. Protected benzophenone intermediate 19 is prepared via an aldol-elimination reaction followed by a PtO2-catalyzed asymmetric hydrogenation. Two routes leading from 19 to compounds 2 and 3 are evaluated. The application of 3 as an activity-based probe has been demonstrated by localizing γ-secretase activity in the plasma membrane of intact cells.

Diastereoselective reduction of a chiral N-Boc-protected δ-amino-α,β-unsaturated γ-keto ester Phe-Gly dipeptidomimetic

The readily available N-Boc-protected δ-amino α,β-unsaturated γ-keto ester 1 was diastereoselectively reduced to the corresponding alcohols 2 and 3, using boron- and aluminum-based reducing reagents. Reduction reactions were successful and resulted in anti/syn ratios of alcohols of >95:5 (80% yield), using LiAlH(O-t-Bu)3 in EtOH at -78 °C under chelation control, and 5:95 (98% yield), using NB-Enantride in THF at -78 °C under Felkin-Anh control.