799270-24-9

Upstream product

• 223526-67-8 (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid 
• 328086-61-9 ethyl (S,E)-4-((tert-butoxycarbonyl)amino)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate 
• 72-18-4 L-valine 
• 94914-66-6 (S)-2-dibenzylamino-3-methylbutanoic acid 
• 862414-80-0 (2R,5S)-methyl 5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 328273-02-5 (2R,5S)-methyl 5-(benzyloxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 1426814-56-3 (R)-methyl 2-bromo-3-(4-fluorophenyl)propanoate 
• 328273-06-9 C₁₆H₂₂FNO₃ 
• 1426814-68-7 (2R)-2-bromo-3-(4-fluorophenyl)propanoic acid 
• 56-86-0 L-glutamic acid 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 59279-60-6 dimethyl (2S)-2-[(tert-butoxycarbonyl)amino]pentanedioate 
• 18125-46-7 (R)-4-fluorophenylalanine 
• 191731-16-5 (S)-tert-butyl 4-(benzyloxycarbonyl)amino-5-methyl-3-oxohexanoate 

Relevant academic research and scientific papers

Improved synthesis of rupintrivir

An improved synthesis of rupintrivir (AG7088) was accomplished using three amino acids (l-glutamic acid, d-4-fluorophenylalanine, and l-valine) as the building blocks. The key fragment ketomethylene dipeptide isostere was constructed with the valine derivative and phenylpropionic acid derivative, followed by coupling with a lactam derivative and an isoxazole acid chloride to provide AG7088 totally in eight steps.

An efficient and tunable route to AG7088, a rhinovirus protease inhibitor

Aldol reaction of N,N-dibenzyl valinal with propiolic acid ethyl ester derived lithium reagent provides anti-aminoalcohol 8 and syn-aminoalcohol 9, which are converted into the lactone 6 via two different routes. Alkylation of 6 followed by lactone ring o