64896-37-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-Methyl 2-((tert-butoxycarbonyl)aMino)pentanoate is used as an intermediate in the synthesis of pharmaceuticals for its ability to be incorporated into complex molecular structures. Its protected amine group allows for selective reactions, making it a valuable building block in the development of new drugs.
Used in Antiviral Applications:
(S)-Methyl 2-((tert-butoxycarbonyl)aMino)pentanoate is used as a potential antiviral agent for preventing or treating infections caused by Pneumovirinae viruses. Its specific structure may interact with viral components or host cell receptors, thereby inhibiting viral replication or attachment, which can help in managing or preventing such infections.

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 56558-30-6 methyl L-norvalinate hydrochloride 
• 53308-95-5 N-tert-butoxycarbonyl-L-norvaline 
• 74-88-4 methyl iodide 
• 1239606-51-9 tert-butyl (S)-1-(methoxycarbonyl)buta-2,3-dienylcarbamate 
• 107-05-1 3-chloroprop-1-ene 
• 162007-08-1 methyl (2S)-(tert-butoxycarbonylamino)-5-iodopentanoate 
• 917-54-4 methyllithium 
• 76969-87-4 tert-Butyloxycarbonyl-L-α-amino-γ-bromobutyric acid methyl ester 
• 142729-70-2 D,L-N-Boc-nor-valine methyl ester 
• 186581-53-3 diazomethane 
• 76969-87-4 methyl (2S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 101650-17-3 (S)-2-amino-4-bromobutyric acid methyl ester 

Downstream Products

• 160801-74-1 (2S)-2-(1,1-dimethylethoxycarbonylamino)pentanal 
• 1158971-62-0 1,1-dimethylethyl {(1S)-1-[bis(4-fluorophenyl)(hydroxy)methyl]butyl}carbamate 

Relevant academic research and scientific papers

Synthesis of ω-Oxo Amino Acids and trans-5-Substituted Proline Derivatives Using Cross-Metathesis of Unsaturated Amino Acids

A range of 7-oxo, 8-oxo, and 9-oxo amino acids, analogues of 8-oxo-2-aminodecanoic acid, one of the key components of the cyclic tetrapeptide apicidin, have been prepared by a three-step process involving copper-catalyzed allylation of serine-, aspartic acid-, and glutamic acid-derived organozinc reagents, followed by cross-metathesis of the resulting terminal alkenes with unsaturated ketones and hydrogenation. The intermediate 7-oxo-5-enones underwent a highly diastereoselective (dr ≥96:4) acid-catalyzed aza-Michael reaction to give trans-2,5-disubstituted pyrrolidines, 5-substituted proline derivatives. The aza-Michael reaction was first observed when the starting enones were allowed to stand in solution in deuterochloroform but can be efficiently promoted by catalytic amounts of dry HCl.

Oxazolidinones and 2,5-Dihydrofurans via Zinc-Catalyzed Regioselective Allenylation Reactions of l -α-Amino Aldehydes

The simultaneous control of diastereoselectivity and regioselectivity in Zn-catalyzed allenylation reactions of N-protected l-α-amino aldehydes is reported. A reversal in diastereoselectivity could be realized by variation of the α-amino aldehyde protecti

Bioproduction of l-2-Aminobutyric Acid by a Newly-Isolated Strain of Aspergillus tamarii ZJUT ZQ013

Abstract: l-2-Aminobutyric acid (l-ABA), an unnatural amino acid, is a key intermediate of several important drugs. Although some methods have been developed to prepare pure chiral l-ABA, there are still many drawbacks, including low catalytic efficiency, cumbersome steps and high cost due to the addition of some expensive catalysts or coenzymes. Herein, with chemical and biological approaches together, we discovered a newly isolated Aspergillus tamarii ZJUT ZQ013 strain containing a microbial lipase which could be employed to resolve racemic methyl N-Boc-2-aminobutyrate to produce l-ABA with high enantioselectivity (e.e.s?>?99.9%, E = 257). Moreover, the subsequent gram scale experiment confrimed that A. tamarii ZJUT ZQ013 could be an attractive biocatalyst for the efficient preparation of optically pure acid. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis of optically active α-(allenyl)-and a-substituted-α- (allenyl)glycines

The synthesis of various types of optically active α-(allenylsilane- containing)glycines via a chiralitytransferring ester-enolate Claisen rearrangement of α-acyloxy-a-alkynylsilanes is described. The conversion of the rearranged products into the optically active silicon-free α-(allenyl)-and α-substituted-α-(allenyl)glycines was achieved by the removal of the Me2PhSi-or TMS group from the allene terminus.

Discovery of tetrasubstituted imidazolines as potent and selective neuropeptide Y Y5 receptor antagonists: Reduced human ether-a-go-go related gene potassium channel binding affinity and potent antiobesity effect

A series of novel imidazoline derivatives was synthesized and evaluated as neuropeptide Y (NPY) Y5 receptor antagonists. Optimization of previously reported imidazoline leads, 1a and 1b, was attempted by introduction of substituents at the 5-position on the imidazoline ring and modification of the bis(4-fluorphenyl) moiety. A number of potent derivatives without human ether-a-go-go related gene potassium channel (hERG) activity were identified. Selected compounds, including 2a, were shown to have excellent brain and CSF permeability. Compound 2a displayed a suitable pharmacokinetic profile for chronic in vivo studies and potently inhibited D-Trp34NPY-induced acute food intake in rats. Oral administration of 2a resulted in a potent reduction of body weight in a diet-induced obese mouse model.

Enzymatic approach to both enantiomers of N-Boc hydrophobic amino acids

Protease catalysed hydrolysis of N-Boc-amino acid esters allows us to obtain N-Boc l-acids and d-esters of amino butanoic acid, nor-leucine, nor-valine, leucine and t-leucine in excellent ee. The reaction occurs in short reaction times and high concentrations. When a biphasic system (buffer-MTBE) is employed, a strong solvent effect is observed. This method could be of significance for the preparation of d-t-leucine, for which a practical method is currently unavailable.

Exploration of acyl sulfonamides as carboxylic acid replacements in protease inhibitors of the hepatitis C virus full-length NS3

The hepatitis C virus (HCV) NS3 protease has emerged as a promising anti-HCV drug target. Herein, we present an investigation of NS3 inhibitors comprising the acyl sulfonamide functionality. A series of tetra- and tripeptide based acyl sulfonamide inhibit

LES ORGANOCUPRATES DANS UNE NOUVELLE SYNTHESE D'AMINOACIDES ENANTIOMERIQUEMENT PURS

A new general method of synthesis of optically pure α- amino esters was elaborated during studies on the reaction of organocuprates with tosyl and halogeno derivatives of L-serine and L-homoserine.

ORGANOCUPRATES MEDIATED CARBON-CARBON BOND FORMATION IN γ POSITION OF α-AMINO ESTERS WITHOUT RACEMISATION

A new general method of synthesis of optically pure α-amino esters by action of organocuprates on t-butyloxycarbonyl-L-α-amino-γ-bromobutyric acid methyl ester is described.

LITHIUM DIORGANOCUPRATE REACTIONS WITH L-SERINE DERIVATIVES

The lithium diorganocuprate reactions with L-serine derivatives are studied.Retention of configuration, or at least a high enantiomeric excess (> 80percent) of the formed α-amino esters is observed in all cases.Attempts are made to restrict side-reactions.