21685-17-6

Usage

Uses

Used in Organic Synthesis:
(R)-(-)-norvaline methyl ester is used as a building block in organic synthesis for the preparation of peptide and protein analogues, leveraging its chiral nature to create complex molecular structures.
Used in Pharmaceutical Development:
(R)-(-)-norvaline methyl ester is used as a key component in the development of pharmaceuticals, where its chirality plays a crucial role in the synthesis of enantiomerically pure drugs, enhancing the efficacy and safety of medications.
Used in Agrochemical Development:
(R)-(-)-norvaline methyl ester is used as a precursor in the synthesis of chiral agrochemicals, contributing to the development of more effective and targeted pesticides and herbicides.
Used in Enzyme-Catalyzed Reactions:
(R)-(-)-norvaline methyl ester is used in the study of enzyme-catalyzed reactions, providing insights into the stereoselectivity of enzymatic processes and aiding in the understanding of biological mechanisms.
Used in Medical Research:
(R)-(-)-norvaline methyl ester is used in medical research for the design and development of new drugs and therapeutic agents, capitalizing on its chiral properties to create innovative and effective treatments for various diseases and conditions.

Upstream product

• 87974-74-1 (R)-2-[(1S,2S,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pentanoic acid methyl ester 
• 476689-69-7 (1R)-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(4-methoxyanilino)-4-pentenoate 
• 476689-71-1 (1R)-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(4-methoxyanilino)pentanoate 
• 51220-50-9 methyl (3R)-aminopentanoate 
• 2013-12-9 D-norvaline 
• 67-56-1 methanol 
• 476689-72-2 (2R)-2-(4-methoxyanilino)pentanoic acid 
• 476689-73-3 methyl (2R)-2-(4-methoxyanilino)pentanoate 
• 87974-74-1 (R)-2-[(1S,2R,5S)-2-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-(3E)-ylideneamino]-pentanoic acid methyl ester 

Downstream Products

• 1314228-04-0 (R)-methyl 1-tosylpyrrolidine-2-carboxylate 
• 51220-82-7 (S)-methyl 2-(4-methylphenylsulfonamido)pentanoate 
• 2013-12-9 D-norvaline 

Relevant academic research and scientific papers

Structure-Guided Design and Development of Potent and Selective Dual Bromodomain 4 (BRD4)/Polo-like Kinase 1 (PLK1) Inhibitors

The simultaneous inhibition of polo-like kinase 1 (PLK1) and BRD4 bromodomain by a single molecule could lead to the development of an effective therapeutic strategy for a variety of diseases in which PLK1 and BRD4 are implicated. Compound 23 has been found to be a potent dual kinase-bromodomain inhibitor (BRD4-BD1 IC50 = 28 nM, PLK1 IC50 = 40 nM). Compound 6 was found to be the most selective PLK1 inhibitor over BRD4 in our series (BRD4-BD1 IC50 = 2579 nM, PLK1 IC50 = 9.9 nM). Molecular docking studies with 23 and BRD4-BD1/PLK1 as well as with 6 corroborate the biochemical assay results.

Exciton-Coupled Circular Dichroism Characterization of Monotopically Binding Guests in Host?Guest Complexes with a Bis(zinc porphyrin) Tweezer

A stiff-stilbene-linked bisporphyrin tweezer with inherent helicity was used for exciton-coupled circular dichroism (ECCD) characterization of a series of monotopically binding amine guest molecules. CD signals were observed for a variety of monoamines at relatively low tweezer/amine (host/guest) ratios between 1 : 10 to 1 : 70. For the amines producing the most intense CD signals, a binding stoichiometry of 1 : 2 was found. A likely explanation is the presence of guest-guest interactions in the complexes. This is supported by the correlation observed between CD signal intensity and magnitude of possible noncovalent binding between the guests, which can be divided into three groups showing no, moderate and strong response, respectively. Further support for this rationalization comes from molecular modelling.

Synthesis of enantiopure cyclic amino acid derivatives via a sequential diastereoselective Petasis reaction/ring closing olefin metathesis process

A novel approach to the synthesis of enantiopure cyclic amino esters is reported. The utilization of allylboronic acid together with (S)-α-methylbenzylamine as a chiral auxiliary in the Petasis/Mannich reaction led to the formation of allylglycine derivatives in good yield and with high diastereoselectivity. Subsequent esterification, N-allylation followed by ring-closing metathesis (RCM) reaction enabled the preparation of enantiomerically pure cyclic α-amino acid derivatives.

Polycyclic Azetidines and Pyrrolidines via Palladium-Catalyzed Intramolecular Amination of Unactivated C(sp3)-H Bonds

A novel strategy to construct complex polycyclic nitrogen-containing heterocycles from aliphatic amines via picolinamide-assisted palladium-catalyzed C-H bond activation reaction was reported. The reaction exhibits broad substrate scope for the synthesis of various azabicyclic scaffolds, including azetidines and tropane-class alkaloids. Application of this method to naturally occurring (-)-cis-myrtanylamine, an unprecedented type of carbon-carbon bond activation, in which the electron-pair involved initiates an intramolecular "SN2-like" displacement of a cyclopalladium-fragment from a tertiary center, is described.

Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

Mechanistic evidence observed in Hofmann-L?ffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity. (Chemical Equation Presented).

Anthranilimide-based glycogen phosphorylase inhibitors for the treatment of Type 2 diabetes: 2. Optimization of serine and threonine ether amino acid residues

Optimization of the amino acid residue of a series of anthranilimide-based glycogen phosphorylase inhibitors is described leading to the identification of serine and threonine ether analogs. t-Butylthreonine analog 20 displayed potent in vitro inhibition of GPa, low potential for P450 inhibition, and excellent pharmacokinetic properties.

PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE AMINOPENTANE DERIVATIVE, INTERMEDIATE IN THE PROCESS AND PROCESS FOR PRODUCTION OF THE INTERMEDIATE

[PROBLEMS] To provide: a process for producing an optically active aminopentane derivative which is expected to be useful as a psychotropic agent, an antidepressant, an anti-Perkinson agent, an anti-Alzhemer disease, an anti-apoptotic agent or the like; a novel optically active intermediate oxathiazolidine derivative which is quite useful for the production of the aminopentane derivative; and a process for producing the intermediate. [MEANS FOR SOLVING PROBLEMS] An optically active aminopentane derivative can be produced in an industrially advantageous manner from a novel optically active oxathiazolidine derivative represented by the formula (5): (5) wherein * represents the position of an asymmetric carbon atom either in R-configuration or S-configuration; and n represents 0 or 1.

Novel stereocontrolled addition of allylmetal reagents to α-imino esters: Efficient synthesis of chiral tetrahydroquinoline derivatives

To prepare in multigram scale new antagonists of the glycine binding site associated to the NMDA receptor, an efficient distereoselective route was set up. The addition of suitable allyltin reagents to chiral N-aryl α-imino esters (R-(+)-tert-butyl lactate used as chiral auxiliary), gave the corresponding α amino acid-type derivative in high chemical yield and optical purity. This allylation reaction represents a novel example of efficient long-range stereodifferentiation process. In the last part of the synthesis, a regioselective Heck-type cyclization reaction enabled preparation of the target tetrasubstituted exocycle and trisubtituted endocycle double bond derivatives.

Chemo-enzymatic synthesis of optically active amino acids and peptides

The industrial alkaline protease, alcalase, is stable and active in a high concentration of organic solvents and useful as a biocatalyst for (i) diastereoselective hydrolysis of peptide esters and preparation of racemization-free peptides; (ii) selective incorporation of esters of D-amino acid into peptides in t-butanol via a selective hydrolysis of esters of D,L-amino acid, followed by using the unhydrolyzed D-esters as a nucleophile in a kinetically controlled peptide bond formation; (iii) resolution of esters of amino acid in 95% t-butanol/5% water, followed by saponification of the unreacted esters to offer both enantiomers with high yield and optical purity; (iv) completely resolve amino-acid esters with high yield and optical purity via in situ racemization of the unreacted antipode catalyzed by pyridoxal 5-phosphate; (v) cryobioorganic synthesis of peptides with increased yields 15%-40% of peptide bond formation by reaction at 5 °C instead of 25-30 °C of a kinetically controlled enzymatic reaction in alcohols.

Diastereoselective protonation of enolates of chiral Schiff bases

Diastereoselective protonation of potassium enolates of chiral Schiff bases prepared from racemic α-amino esters and 2-hydroxypinan-3-one afforded, after mild cleavage of the imine function, optically active α- amino esters.