623582-51-4

Usage

Uses

Used in Medicinal Chemistry:
(3R,4R)-4-(((benzyloxy)carbonyl) amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid is used as a building block for the synthesis of complex organic molecules and pharmaceutical compounds. Its unique structural features and functional groups make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Drug Discovery:
In the field of drug discovery, (3R,4R)-4-(((benzyloxy)carbonyl) amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid is utilized as a potential lead compound. Its specific stereochemistry and protective groups can be exploited to explore novel biological activities and target specific receptors or enzymes in the human body.
Used in Peptide Synthesis:
(3R,4R)-4-(((benzyloxy)carbonyl) amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid is employed as a key component in the synthesis of peptides and peptide-based drugs. Its protected amine groups facilitate the stepwise assembly of peptide chains, while the carboxylic acid group allows for further functionalization and conjugation to other molecules.
Further research and development are necessary to fully understand and harness the chemical properties and potential uses of (3R,4R)-4-(((benzyloxy)carbonyl) amino)-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid in various industries.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 1033881-75-2 (3R,4R)-4-(benzyloxycarbonylamino)pyrrolidine-3-carboxylic acid 
• 623582-43-4 1-(2-hydroxy-1-phenyl-ethyl)-tetrahydro-pyrrolo[3,4-c]isoxazole-5-carboxylic acid tert-butyl ester 
• 1184918-34-0 (3R,4R)-3-amino-4-hydroxymethyl-N-t-butoxycarbonylpyrrolidine 
• 251948-88-6 N-allyl-N-(tert-butyloxycarbonyl)-glycinal 
• 501-53-1 benzyl chloroformate 
• 31954-27-5 N-(tert-butoxycarbonyl)glycine methyl ester 
• 116613-80-0 N-allyl-N-(tert-butoxycarbonyl)glycine methyl ester 
• 623582-53-6 (3R,4R)-tert-butyl 3-(benzyloxycarbonyl)amino-4-(hydroxymethyl)pyrrolidine-1-carboxylate 

Downstream Products

• 369623-85-8 (3R,4R)-4-Amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 
• 1033881-79-6 (3R,4R)-tert-butyl 3-(benzyloxycarbonylamino)-4-((3S)-1-(2-((S)-2-(dimethylamino)-2-oxo-1-phenylethylamino)-2-oxoethylamino)-2-hydroxy-1-oxohexan-3-ylcarbamoyl)pyrrolidine-1-carboxylate 
• 1422561-07-6 C₂₂H₂₉N₃O₅ 
• 1422561-10-1 C₂₅H₃₃N₃O₇ 
• 1422561-09-8 (3R,4R)-tert-butyl 3-(((benzyloxy)carbonyl)amino)-4-(4,5-dimethyloxazol-2-yl)pyrrolidine-1-carboxylate 
• 1001054-84-7 C₂₃H₃₂N₄O₆ 
• 1001054-83-6 C₂₂H₃₁N₃O₅ 

Relevant academic research and scientific papers

Novel α- and β-amino acid inhibitors of influenza virus neuraminidase

In an effort to discover novel, noncarbohydrate inhibitors of influenza virus neuraminidase we hypothesized that compounds which contain positively charged amino groups in an appropriate position to interact with the Asp 152 or Tyr 406 side chains might be bound tightly by the enzyme. Testing of 300 α- and β-amino acids led to the discovery of two novel neuraminidase inhibitors, a phenylglycine and a pyrrolidine, which exhibited Ki values in the 50 μM range versus influenza virus A/N2/Tokyo/3/67 neuraminidase but which exhibited weaker activity against influenza virus B/Memphis/3/89 neuraminidase. Limited optimization of the pyrrolidine series resulted in a compound which was about 24-fold more potent than 2-deoxy-2,3-dehydro-N-acetylneuraminic acid in an anti-influenza cell culture assay using A/N2/Victoria/3/75 virus. X-ray structural studies of A/N9 neuraminidase-inhibitor complexes revealed that both classes of inhibitors induced the Glu 278 side chain to undergo a small conformational change, but these compounds did not show time-dependent inhibition. Crystallography also established that the α-amino group of the phenylglycine formed hydrogen bonds to the Asp 152 carboxylate as expected. Likewise, the β-amino group of the pyrrolidine forms an interaction with the Tyr 406 hydroxyl group and represents the first compound known to make an interaction with this absolutely conserved residue. Phenylglycine and pyrrolidine analogs in which the α- or β-amino groups were replaced with hydroxyl groups were 365- and 2,600-fold weaker inhibitors, respectively. These results underscore the importance of the amino group interactions with the Asp 152 and Tyr 406 side chains and have implications for anti-influenza drug design.

HCV PROTEASE INHIBITORS AND USES THEREOF

This invention relates to: (a) compounds of formula I and salts thereof that, inter alia, are useful as hepatitis C virus (HCV) inhibitors; (b) intermediates useful for the preparation of such compounds and salts; (c) pharmaceutical compositions comprising such compounds and salts; and (d) methods of use of such compounds, salts, and compositions.

Synthesis of Cyclic and Acyclic β-Amino Acids via Chelation-Controlled 1,3-Dipolar Cycloaddition

Isoxazolidines have been synthesized in diastereomeric excess up to 94% via a MgBr2-induced chelation-controlled 1,3-dipolar cycloaddition reaction with N-hydroxyphenylglycinol as a chiral auxiliary. The diastereomerically pure isoxazolidines were further transformed into cyclic and acyclic β-amino acid derivatives.