191731-16-5

Usage

Uses

Used in Pharmaceutical Research and Development:
Tert-Butyl (S)-4-(Cbz-amino)-5-methyl-3-oxohexanoate is used as a reagent in the production of peptide-based drugs, serving as a building block for various pharmaceuticals. Its protective role for amino groups is crucial in the synthesis of complex peptide structures, ensuring the successful formation of desired compounds.
Used in Organic Synthesis:
In the field of organic synthesis, tert-Butyl (S)-4-(Cbz-amino)-5-methyl-3-oxohexanoate is utilized for its ability to protect amino groups during reactions, allowing for the creation of a wide range of organic compounds with specific functionalities.
Used in the Development of New Synthetic Methods:
tert-Butyl (S)-4-(Cbz-amino)-5-methyl-3-oxohexanoate is also employed in the development of innovative synthetic methods, contributing to the advancement of chemical processes and techniques in the field of chemistry.
Used in the Preparation of Reference Standards for Analytical Testing:
Tert-Butyl (S)-4-(Cbz-amino)-5-methyl-3-oxohexanoate is used in the preparation of reference standards, which are essential for the accurate analysis and testing of various chemical and pharmaceutical products, ensuring their quality and consistency.

InChI:InChI=1/C19H27NO5/c1-13(2)17(15(21)11-16(22)25-19(3,4)5)20-18(23)24-12-14-9-7-6-8-10-14/h6-10,13,17H,11-12H2,1-5H3,(H,20,23)/t17-/m0/s1

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 1207973-75-8 lithium tert-butyl acetate 
• 540-88-5 acetic acid tert-butyl ester 
• 24210-19-3 methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 202806-77-7 t-butyl-(3R,4S)-4-(N-benzyloxycarbonylamino)-3-hydroxy-5-methyl-hexanoate 
• 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 
• 362610-31-9 (3-bromo-1-(S)-(1-methylethyl)-2-oxopropyl)carbamic acid benzyl ester 
• 151011-85-7 (2R,5S)-2-Benzyl-5-tert-butoxycarbonylamino-6-methyl-4-oxo-heptanoic acid 

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.

Inhibition of the severe acute respiratory syndrome 3CL protease by peptidomimetic α,β-unsaturated esters

The proteolytic processing of polyproteins by the 3CL protease of severe acute respiratory syndrome coronavirus is essential for the viral propagation. A series of tripeptide α,β-unsaturated esters and ketomethylene isosteres, including AG7088, are synthesized and assayed to target the 3CL protease. Though AG7088 is inactive (IC50 > 100 μM), the ketomethylene isosteres and tripeptide α,β-unsaturated esters containing both P1 and P2 phenylalanine residues show modest inhibitory activity (IC50 = 11-39 μM). The Phe-Phe dipeptide inhibitors 18a-e are designed on the basis of computer modeling of the enzyme-inhibitor complex. The most potent inhibitor 18c with an inhibition constant of 0.52 μM is obtained by condensation of the Phe-Phe dipeptide α,β-unsaturated ester with 4-(dimethylamino)cinnamic acid. The cell-based assays also indicate that 18c is a nontoxic anti-SARS agent with an EC50 value of 0.18 μM.

An efficient synthesis of γ-amino β-ketoester by cross-Claisen condensation with α-amino acid derivatives

Cross-ester condensation between N-protected amino acid ester and the lithium enolate prepared from alkyl acetate gave the corresponding β-ketoester in high yield without the formation of the tertiary alcohol that is commonly seen as by-product. This inte

Tetrapeptides as antitumor agents

The present invention provides anti-tumor peptides of Formula I, and the acid salts thereof. A is an amino acid residue selected from the group consisting of N-methyl-D-prolyl, N-methyl-D-homoprolyl and N,N-dimethyl-2-ethylphenylglycyl, or an amino ac

Pentapeptides as antitumor agents

The present invention provides anti-tumor peptides of Formula I, and the acid salts thereof. A is an amino acid residue of the formula (CH3)2 N--CHX--CO, wherein X is a normal or branched alkyl group. B is an amino acid residue s

A simple, stereoselective synthesis of ketomethylene dipeptide isosteres

An exceedingly simple, general, and stereoselective method for the preparation of ketomethylene dipeptide isosteres (5-(carbobenzyloxyamino)-2-alkyl-γ-ketoesers) from Cbz-protected amino acids and scalemic-2-triflyloxy esters has been developed. The method is short (three steps), efficient, and highly diastereoselective and enantioselective.