21685-17-6

Basic information

• Product Name: (R)-(-)-norvaline methyl ester
• Synonyms: (R)-(-)-norvaline methyl ester
• CAS NO: 21685-17-6
• Molecular Weight: 131.175
• Mol File: 21685-17-6.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (R)-(-)-norvaline methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-norvaline methyl ester(21685-17-6)
• EPA Substance Registry System: (R)-(-)-norvaline methyl ester(21685-17-6)

Safety Data

• Hazardous Substances Data: 21685-17-6(Hazardous Substances Data)

Usage

Description

(R)-(-)-norvaline methyl ester is a chiral chemical compound derived from the amino acid norvaline, characterized by its non-superimposable mirror image. This unique property makes it a valuable building block in organic synthesis for the preparation of peptide and protein analogues. Its applications extend to the development of pharmaceuticals and agrochemicals, as well as in the study of enzyme-catalyzed reactions, with potential uses in medical research for the design and development of new drugs and therapeutic agents.

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 
• 51220-50-9 methyl (3R)-aminopentanoate 
• 67-56-1 methanol 
• 2013-12-9 D-norvaline 
• 476689-71-1 (1R)-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(4-methoxyanilino)pentanoate 
• 476689-69-7 (1R)-tert-butoxy-1-methyl-2-oxoethyl (2R)-2-(4-methoxyanilino)-4-pentenoate 
• 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 articles and documents

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.

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.

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).