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

General Description

Methyl(R)-N-Boc-3-aminobutyrate is a chemical compound used in organic synthesis and pharmaceutical research. It is a derivative of the amino acid valine, with a methyl group, a Boc protecting group, and an amino group attached to the carbon chain. The Boc protecting group makes it a useful intermediate in the synthesis of peptide and protein-based drugs. It is also used as a chiral building block in the synthesis of various pharmaceuticals and fine chemicals. The compound has potential applications in the development of new drugs and therapeutic agents.

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 
• 139243-54-2 (R)-3-aminobutanoic acid methyl ester hydrochloride 
• 67-56-1 methanol 
• 186521-98-2 N-[(1R)-3-diazo-1-methyl-2-oxopropyl]carbamic acid tert-butyl ester 
• 21731-17-9 methyl 3-aminocrotonate 
• 105-45-3 acetoacetic acid methyl ester 
• 4248-19-5 tert-butyl carbazate 
• 3744-87-4 Boc-(R)-Ala 
• 64838-60-4 (3R,1'S)-3-<(1'-phenylethyl)amino>butanoic acid methyl ester 
• 136703-60-1 (3S)-3-[(tert-butoxycarbonyl)amino]-4-iodobutanoic acid methyl ester 
• 136703-59-8 (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoic acid methyl ester 
• 59768-74-0 (S)-2-t-butoxycarbonylaminosuccinic acid 4-methyl ester 
• 139519-25-8 Boc-L-Asp(β-methyl)-N-hydroxysuccinimide 

Downstream Products

• 159991-23-8 (R)-3-((tert-butoxycarbonyl)amino)butanoic acid 
• 193152-95-3 (2R,3R)-3-tert-Butoxycarbonylamino-2-(3-cyano-benzyl)-butyric acid methyl ester 
• 193152-96-4 (2R,3R)-3-Amino-2-(3-cyano-benzyl)-butyric acid methyl ester 
• 193153-00-3 (2R,3R)-3-[(Biphenyl-4-carbonyl)-amino]-2-(3-cyano-benzyl)-butyric acid methyl ester 
• 159877-48-2 (R)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]butanamide 
• 159877-49-3 (R)-3-[[(1,1-dimethylethoxy)carbonyl]amino]butanethioamide 
• 167216-17-3 (-)-tert-butyl [(R)-3-hydroxy-1-methylpropyl]carbamate 
• 6078-06-4 (R)-methyl 3-aminobutanoate hydrochloride 

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.

Access to 2,6-Disubstituted 4-Oxopiperidines Using a 6-Endo-trig Cyclization: Stereoselective Synthesis of Spruce Alkaloid and (+)-241D

A synthetic route to cis-2-methyl-4-oxo-6-alkylpiperidines has been developed using a 6-endo-trig cyclization of (E)-enones. The base-mediated intramolecular cyclization was found to be general for both alkyl- and aryl-substituted enones, providing the corresponding 4-oxopiperidines in high yields (80-89%). Stereoselective reduction of the 2,6-cis-disubstituted 4-oxopiperidines then gave the 2,4,6-cis,cis-trisubstituted 4-hydroxypiperidines in high diastereoselectivity. The general nature of this approach was demonstrated with the synthesis of the natural products, spruce alkaloid and (+)-241D.

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.