328273-02-5

Basic information

• Product Name: (αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid
• Synonyms: (αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid;methyl (2R,5S)-5-(((benzyloxy)carbonyl)amino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate
• CAS NO: 328273-02-5
• Molecular Formula: C₂₄H₂₈FNO₅
• Molecular Weight: 429.4812232
• Product Categories: Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 328273-02-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: (αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid(328273-02-5)
• EPA Substance Registry System: (αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid(328273-02-5)

Safety Data

• Hazardous Substances Data: 328273-02-5(Hazardous Substances Data)

Usage

Description

(αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid is a complex organic compound characterized by its unique molecular structure and chemical properties. It is a white solid with potential applications in various fields due to its specific functional groups and reactivity.

Uses

Used in Pharmaceutical Industry:
(αR)-α-[(3S)-3-(CarboxybenzylaMino)-4-Methyl-2-oxopentyl]-4-fluoro-benzenepropanoic Acid is used as a key intermediate in the synthesis of rhinovirus protease inhibitors. These inhibitors play a crucial role in the development of antiviral drugs targeting the human rhinovirus, which is a major cause of common cold and other respiratory illnesses.
Additionally, this compound is utilized in the preparation of peptidomimetic α,β-unsaturated esters. Peptidomimetics are a class of molecules that mimic the structure and function of peptides, offering potential applications in drug design and development due to their stability and bioavailability.

Upstream product

• 18125-46-7 (R)-4-fluorophenylalanine 
• 1426814-68-7 (2R)-2-bromo-3-(4-fluorophenyl)propanoic acid 
• 1426814-56-3 (R)-methyl 2-bromo-3-(4-fluorophenyl)propanoate 
• 124980-98-9 (R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate 
• 328273-04-7 (2R)-3-(4-Fluorophenyl)-2-trifluoromethane-sulfonyloxypropionic Acid Methyl Ester 
• 191731-16-5 (S)-tert-butyl 4-(benzyloxycarbonyl)amino-5-methyl-3-oxohexanoate 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 

Downstream Products

• 862414-80-0 (2R,5S)-methyl 5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 328273-06-9 C₁₆H₂₂FNO₃ 
• 799270-24-9 (S,E)-ethyl 4-((2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanamido)-5-((S)-2-oxopyrrolidin-3-yl)pent-2-enoate 
• 223526-67-8 (2R,5S)-5-(tert-butoxycarbonylamino)-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanic acid 
• 862414-84-4 allyl (2R,5S)-2-(4-fluorobenzyl)-6-methyl-5-{[(5-methyl-3-isoxazolyl)carbonyl]amino}-4-oxoheptanoate 
• 862414-82-2 allyl (2R,5S)-5-(tert-butoxycarbonyl)amino-2-(4-fluorobenzyl)-6-methyl-4-oxoheptanoate 
• 328086-55-1 (2R,5S)-2-(4-Fluoro-benzyl)-6-methyl-5-[(5-methyl-isoxazole-3-carbonyl)-amino]-4-oxo-heptanoic acid 

Relevant articles and documents

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.