159877-47-1

Basic information

• Product Name: Methyl(R)-N-Boc-3-aminobutyrate
• Synonyms: (R)-3-[[(1,1-DiMethylethoxy)carbonyl]aMino]butanoic acid Methyl ester;Butanoic acid, 3-[[(1,1-diMethylethoxy)carbonyl]aMino]-, Methyl ester, (R)-;Butanoic acid, 3-[[(1,1-diMethylethoxy)carbonyl]aMino]-, Methyl ester, (3R)-;(R)-N-BOC-3-Aminobutyric acid ethyl ester;methyl (3R)-3-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate;Boc-(R)-3-AMINO-BUTYRIC ACID METHYL ESTER;(R)-Methyl 3-((tert-butoxycarbonyl)amino)butanoate;(R)-3-tert-Butoxycarbonylamino-butyric acid methyl ester
• CAS NO: 159877-47-1
• Molecular Formula: C₁₀H₁₉NO₄
• Molecular Weight: 217.26
• Product Categories: pharmacetical
• Mol File: 159877-47-1.mol
• Article Data: 14

Chemical Properties

• Boiling Point: 302.8±25.0 °C(Predicted)
• Appearance: /
• Density: 1.035±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 11.77±0.46(Predicted)
• CAS DataBase Reference: Methyl(R)-N-Boc-3-aminobutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl(R)-N-Boc-3-aminobutyrate(159877-47-1)
• EPA Substance Registry System: Methyl(R)-N-Boc-3-aminobutyrate(159877-47-1)

Safety Data

• Hazardous Substances Data: 159877-47-1(Hazardous Substances Data)

Usage

Description

Methyl(R)-N-Boc-3-aminobutyrate is a chemical compound derived from the amino acid valine, featuring a methyl group, a Boc protecting group, and an amino group attached to its carbon chain. Methyl(R)-N-Boc-3-aminobutyrate is utilized in organic synthesis and pharmaceutical research, particularly as an intermediate in the synthesis of peptide and protein-based drugs due to its Boc protecting group. Additionally, it serves as a chiral building block in the creation of various pharmaceuticals and fine chemicals, holding potential for the development of new drugs and therapeutic agents.

Uses

Used in Pharmaceutical Research and Development:
Methyl(R)-N-Boc-3-aminobutyrate is used as a chiral building block for the synthesis of pharmaceuticals and fine chemicals, leveraging its unique structural features to contribute to the development of novel drug candidates.
Used in Organic Synthesis:
As an intermediate in organic synthesis, Methyl(R)-N-Boc-3-aminobutyrate is employed for the creation of complex organic molecules, taking advantage of its Boc protecting group to facilitate specific synthetic pathways.
Used in Peptide and Protein-based Drug Synthesis:
Methyl(R)-N-Boc-3-aminobutyrate is used as a key intermediate in the synthesis of peptide and protein-based drugs, where the Boc protecting group plays a crucial role in the selective protection of the amino group during the synthesis process, ensuring the correct formation of peptide bonds and the desired final product.
Used in the Development of New Drugs and Therapeutic Agents:
Methyl(R)-N-Boc-3-aminobutyrate is utilized in the research and development of new drugs and therapeutic agents, capitalizing on its potential to contribute to the discovery of innovative treatments for various diseases and conditions.

Upstream product

• 67-56-1 methanol 
• 186521-98-2 N-[(1R)-3-diazo-1-methyl-2-oxopropyl]carbamic acid tert-butyl ester 
• 954143-61-4 (R)-2-tert-butoxycarbonylaminopropionyl chloride 
• 139519-25-8 Boc-L-Asp(β-methyl)-N-hydroxysuccinimide 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 136703-59-8 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester 
• 136703-60-1 (3S)-3-[(tert-butoxycarbonyl)amino]-4-iodobutanoic acid methyl ester 
• 64838-60-4 (3R,1'S)-3-<(1'-phenylethyl)amino>butanoic acid methyl ester 
• 3744-87-4 Boc-(R)-Ala 
• 105-45-3 acetoacetic acid methyl ester 
• 4248-19-5 tert-butyl carbazate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 21731-17-9 methyl 3-aminocrotonate 
• 139243-54-2 (R)-3-aminobutanoic acid methyl ester hydrochloride 

Downstream Products

• 497861-77-5 (+)-tert-butyl [(R)-1-methyl-3-oxopropyl]carbamate 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 
• 167216-17-3 (-)-tert-butyl [(R)-3-hydroxy-1-methylpropyl]carbamate 
• 159877-49-3 (R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]butanethioamide 
• 159877-48-2 (R)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]butanamide 

Relevant articles and documents

Modulation of the Passive Permeability of Semipeptidic Macrocycles: N- And C-Methylations Fine-Tune Conformation and Properties

Incorporating small modifications to peptidic macrocycles can have a major influence on their properties. For instance, N-methylation has been shown to impact permeability. A better understanding of the relationship between permeability and structure is of key importance as peptidic drugs are often associated with unfavorable pharmacokinetic profiles. Starting from a semipeptidic macrocycle backbone composed of a tripeptide tethered head-to-tail with an alkyl linker, we investigated two small changes: peptide-to-peptoid substitution and various methyl placements on the nonpeptidic linker. Implementing these changes in parallel, we created a collection of 36 compounds. Their permeability was then assessed in parallel artificial membrane permeability assay (PAMPA) and Caco-2 assays. Our results show a systematic improvement in permeability associated with one peptoid position in the cycle, while the influence of methyl substitution varies on a case-by-case basis. Using a combination of molecular dynamics simulations and NMR measurements, we offer hypotheses to explain such behavior.

Stereoselective synthesis of 2,6-: Trans -4-oxopiperidines using an acid-mediated 6- endo-trig cyclisation

An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (-)-solenopsin A.

BICYCLIC PYRIMIDONE COMPOUNDS AS INHIBITORS OF LP-PLA2

The present invention relates to novel pyrimido[1,6-a]pyrimidin-6(2H)-one compounds that inhibit Lp-PLA2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA2, for example atherosclerosis, Alzheimer's disease.