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

General Description

(R)-2-Amino-2-(2-propenyl)propionsaeure-methylester, also known as Methyl (R)-2-amino-3-methylbut-2-enoate, is a chemical compound with a methyl ester functional group and an amino group attached to a chiral center. It is a colorless liquid with a fruity odor and is commonly used as a flavoring agent in food and beverage products. (R)-2-Amino-2-(2-propenyl)propionsaeure-methylester has been studied for its potential pharmaceutical applications, including as a building block in the synthesis of chiral drugs and as a precursor in the production of various chemicals. It is important to handle this chemical with care, as it can be hazardous if not properly managed.

Upstream product

• 71785-58-5 (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(2-methylnaphthyl)-3,6-dihydropyrazin 
• 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 
• 71785-61-0 (3R,6S)-2,5-Dimethoxy-3,6-dimethyl-3-(2-propenyl)-3,6-dihydropyrazin 
• 67-56-1 methanol 
• 144125-67-7 C^α-methyl-D,L-allylglycinamide 
• 120328-90-7 methyl (E)-N-benzylidenealaninate 
• 106-95-6 allyl bromide 
• 88820-80-8 N-(6-Deoxy-1,2;3,4-di-O-cyclohexyliden-α-D-galactopyranosyliden)alanin-methylester 
• 420-37-1 trimethoxonium tetrafluoroborate 

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.