71785-67-6

Usage

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

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

Relevant academic research and scientific papers

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.

COMBINATION OF HEPATITIS B VIRUS (HBV) VACCINES AND PYRIDOPYRIMIDINE DERIVATIVES

Therapeutic combinations of hepatitis B virus (HBV) vaccines and a pyridopyrimidine derivative are described. Methods of inducing an immune response against HBV or treating an HBV-induced disease, particularly in individuals having chronic HBV infection, using the disclosed therapeutic combinations are also described. The invention provides therapeutic combinations or compositions and methods for inducing an immune response against hepatitis B viruses (HBV) infection.

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.

TOLL LIKE RECEPTOR MODULATOR COMPOUNDS

The present disclosure relates generally to toll like receptor modulator compounds, such as diamino pyrido[3,2 D]pyrimidine compounds and pharmaceutical compositions which, among other things, modulate toll-like receptors (e.g. TLR-8), and methods of making and using them.

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.

Synthesis of (Optically Active) Sulfur-Containing Trifunctional Amino Acids by Radical Addition to (Optically Active) Unsaturated Amino Acids

Sulfur-based radicals, generated from R-S-H-type precursors (R = alkyl, acyl) with AIBN, smoothly add to α-allylglycines protected at none, one, or both of the amino acid functions (NH2 and/or CO2H).Sulfur-containing trifunctional amino acids were obtained in good to excellent yields (64-100 percent).The solvent used for the reaction is critical.Optimal results were obtained when both the unsaturated amino acid and RSH dissolve completely in the medium (dioxane/water or methanol/water are good solvent systems).The scope of the reaction includes α-substituted α-allylglycine derivative and derivatives as well as β-substituted β-allyl-β-amino alcohols.In the case of optically active α-allylglycine derivatives, radical addition is accompanied by a small amount of racemization, the amount depending on the type of protection and R-S-H.The products are easily optically enriched by crystallization.Addition of sulfur-based radicals to α-allylglycine is believed to be an example of a general method for synthesizing optically active trifunctional amino acids from unsaturated amino acids.

ENANTIOSELECTIVE SYNTHESIS OF NON-PROTEINOGENIC AMINO ACIDS VIA METALLATED BIS-LACTIM ETHERS OF 2,5-DIKETOPIPERAZINES

Bis-lactim ethers 1 of 2,5-diketopiperazines contain a chiral inducing center, an acidic CH-bond and two sites susceptible to hydrolysis.They react with BuLi to give Li compounds of type 4, 15, 29 or 32, which possess a prochiral C atom.They readily add electrophiles (such as alkylating agents or carbonyl compounds) with unusually high diastereoface differentiation.In many cases the d.e-value (d.e. = diastereomeric excess = asymmetric induction) of the adduct exceeds 95percent.On hydrolysis the adducts are cleaved liberating the chiral auxiliary (used to build up the bis-lactim ether 1) and the target molecules, the optically active amino acid methyl esters of type 8, 19, 25 or 36.The two amino acid esters are separable either by fractional distillation or (eventually after further hydrolysis to amino acids) by chromatography.Transition state models are discussed that could explain the exceptionally high asymmetric induction and the predictability of the induced configuration.

Asymmetric Syntheses via Heterocyclic Intermediates, V. - Asymmetric Synthesis of α-Methyl Amino Acids by Alkylation of the Lithiated Lactim Ether of cyclo-(L-Ala-L-Ala)

The (3S,6S)-2,5-dimethoxy-3,6-dimethyl-3,6-dihydropyrazine (7) is obtained from cyclo-(L-Ala-L-Ala) 5 (93-95percent optically pure) and trimethyloxonium tetrafluoroborate.With butyllithium the lithio derivative 8 is formed which reacts with alkyl halides in good chemical yields and with more than 90percent diastereoselectivity, whereby R-configuration is induced at C-3.A model concept is discussed, which explains the remarkably high asymmetric induction. - Hydrolysis (0.25 N HCl, room temp.) gives L-alanine methyl ester (4) and the (R)-α-methyl amino acid methyl esters 13.The two amino acid esters are separable by distillation or chromatography.