71785-67-6

Basic information

• Product Name: (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester
• Synonyms: (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester
• CAS NO: 71785-67-6
• Molecular Weight: 143.186
• Mol File: 71785-67-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 154.1±28.0 °C(Predicted)
• Density: 0.978±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester(71785-67-6)
• EPA Substance Registry System: (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester(71785-67-6)

Safety Data

• Hazardous Substances Data: 71785-67-6(Hazardous Substances Data)

Usage

Description

(R)-2-Amino-2-(2-propenyl)propionsaeure-methylester, also known as Methyl (R)-2-amino-3-methylbut-2-enoate, is a chemical compound characterized by a methyl ester functional group and an amino group attached to a chiral center. This colorless liquid with a fruity odor is widely recognized for its applications in the flavor and fragrance industry, as well as its potential pharmaceutical uses.

Uses

Used in Flavor and Fragrance Industry:
(R)-2-Amino-2-(2-propenyl)propionsaeure-methylester is used as a flavoring agent for its distinctive fruity odor, adding a pleasant aroma to various food and beverage products.
Used in Pharmaceutical Applications:
(R)-2-Amino-2-(2-propenyl)propionsaeure-methylester serves as a building block in the synthesis of chiral drugs, contributing to the development of new medications with improved efficacy and selectivity.
Used in Chemical Production:
(R)-2-Amino-2-(2-propenyl)propionsaeure-methylester also acts as a precursor in the production of various chemicals, highlighting its versatility and importance in the chemical industry.
Safety Note:
It is crucial to handle (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester with care due to its potential hazards if not properly managed. Appropriate safety measures should be taken to ensure the safe use and handling of this chemical compound.

Upstream product

• 67-56-1 methanol 
• 144125-67-7 C^α-methyl-D,L-allylglycinamide 
• 124-41-4 sodium methylate 
• 288617-71-0 (R)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-enoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 106-95-6 allyl bromide 
• 71785-61-0 (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(2-propenyl)-3,6-dihydropyrazin 
• 88820-80-8 N-(6-Deoxy-1,2;3,4-di-O-cyclohexyliden-α-D-galactopyranosyliden)alanin-methylester 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 71785-58-5 (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(2-methylnaphthyl)-3,6-dihydropyrazin 

Relevant articles and documents

Discovery of GS-9688 (Selgantolimod) as a Potent and Selective Oral Toll-Like Receptor 8 Agonist for the Treatment of Chronic Hepatitis B

Toll-like receptor 8 (TLR8) recognizes pathogen-derived single-stranded RNA fragments to trigger innate and adaptive immune responses. Chronic hepatitis B (CHB) is associated with a dysfunctional immune response, and therefore a selective TLR8 agonist may be an effective treatment option. Structure-based optimization of a dual TLR7/8 agonist led to the identification of the selective TLR8 clinical candidate (R)-2-((2-amino-7-fluoropyrido[3,2-d]pyrimidin-4-yl)amino)-2-methylhexan-1-ol (GS-9688, (R)-7). Potent TLR8 agonism (IL-12p40 EC50 = 220 nM) and >100-fold TLR7 selectivity (IFN-α EC50 > 50 μM) was observed in human peripheral blood mononuclear cells (PBMCs). The TLR8-ectodomain:(R)-7 complex confirmed TLR8 binding and a direct ligand interaction with TLR8 residue Asp545. Oral (R)-7 had good absorption and high first pass clearance in preclinical species. A reduction in viral markers was observed in HBV-infected primary human hepatocytes treated with media from PBMCs stimulated with (R)-7, supporting the clinical development of (R)-7 for the treatment of CHB.

Quaternized α,α′-Amino Acids via Curtius Rearrangement of Substituted Malonate-Imidazolidinones

An efficient synthesis protocol is presented for accessing quaternized α-amino acids in chiral, nonracemic form via diastereoselective malonate alkylation followed by C- to N-transposition. The key stereodifferentiating step involves a diastereoselective alkylation of an α-monosubstituted malonate-imidazolidinone, which is followed first by a chemoselective malonate PMB ester removal and then a Curtius rearrangement to provide the transposition. The method demonstrates a high product ee (89-99% for eight cases) for quaternizing a range of proteinogenic α-amino acids. The stereogenicity in targets 5a-i supports previous conclusions that the diastereoselective alkylation step proceeds via an α-substituted malonate-imidazolidinone enolate in its Z-configuration, with the auxiliary in an s-transC-N conformation.

A practical asymmetric synthesis of α-methyl α-amino acids using a chiral cu-salen complex as a phase transfer catalyst

The asymmetric C-alkylation of N-benzylidene alanine methyl ester has been achieved using a copper(II) (salen) complex as an asymmetric phase transfer catalyst and provides a practical synthesis of α-methyl α-amino acids with up to 86% enantiomeric excess. (C) 2000 Elsevier Science Ltd.