147383-98-0

Usage

Uses

Used in Pharmaceutical Synthesis:
(2S)-(+)-3,4-dimethoxyphenylglycine is used as a key intermediate in the synthesis of various pharmaceuticals and bioactive molecules, contributing to the development of new drugs and therapies.
Used in Medicinal Chemistry:
As a chiral building block, (2S)-(+)-3,4-dimethoxyphenylglycine is utilized in the production of asymmetric catalysts, which are essential in the synthesis of enantiomerically pure compounds, a critical aspect in medicinal chemistry.
Used in Organic Synthesis:
(2S)-(+)-3,4-dimethoxyphenylglycine serves as a ligand in asymmetric catalysis, a technique that is vital for the selective synthesis of specific enantiomers in organic chemistry, which is crucial for the production of biologically active compounds.
Used in Neuroprotection and Antioxidant Research:
(2S)-(+)-3,4-dimethoxyphenylglycine is studied for its potential neuroprotective and antioxidant properties, indicating its possible use in the development of treatments for neurological disorders and conditions associated with oxidative stress.

Upstream product

• 1141846-94-7 C₁₈H₁₉NO₅ 
• 1141847-01-9 C₁₅H₁₉NO₇ 
• 250665-92-0 [2S,1'S,2'S]-(+)-2-(3,4-dimethoxyphenyl)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 
• 234089-44-2 (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-2-(3,4-dimethoxyphenyl)-N-methylacetamide 
• 250665-97-5 [2S,1'S,2'S]-(+)-2-amino-2-(3,4-dimethoxyphenyl)-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methylacetamide 

Downstream Products

• 394739-96-9 (2S)-(-)-2-[(E)-2,3-dimethoxybenzylideneamino]-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-97-0 (2S)-(+)-2-(2,3-dimethoxybenzyl)amino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-98-1 (2S)-(+)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-dimethoxyphenyl)ethanol 
• 394739-99-2 (3S,4S)-(+)-7,8-dimethoxy-3-(3,4-dimethoxyphenyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ol 
• 114673-69-7 (2S)-(+)-2-amino-2-(3,4-dimethoxyphenyl)ethanol 
• 739358-12-4 methyl (2S)-(+)-2-amino-2-(3,4-dimethoxyphenyl)acetate 

Relevant academic research and scientific papers

One-pot, regioselective synthesis of substituted arylglycines for kinetic resolution by penicillin G acylase

Amido-alkylation of electron-rich arenes with phenylacetamide and glyoxylic acid offers an in-expensive route to a large variety of N-phenylacetylated arylglycines that are suited for immediate enzymatic resolution by penicillin G acylase. When performed under mild conditions at 5 °C in acetic acid/HCl, this simple one-pot operation resulted in the formation of single regioisomers only (≥98%). Subsequent kinetic resolution of the amino acid derivatives by penicillin G acylase at pH 8.0 occurred generally with E values >100 and thus furnished free (S)-configurated arylglycines with high enantiomeric purity. The corresponding enantiopure (R)-substrates, easily separable by a phase-selective extraction process, provided the corresponding (R)-enantiomers upon conventional hydrolysis. This one-pot, two-step procedure for arylglycine synthesis, resolution and work-up requires a minimum of equipment and grants rapid access to both enantiopure (S)- and (R)-antipodes of non-natural α-amino acids in small-to large-scale quantities.

Asymmetric synthesis of arylglycines and their use as chiral templates for the stereocontrolled synthesis of 7,8-disubstituted 3-Aryl-1,2,3,4-tetrahydroisoquinolin-4-ols

A synthetic technique for the asymmetric synthesis of arylglycines has been optimized, reaching the target amino acids in only four steps with good yields and with enantiomeric excesses higher than 99%. The key step consisted of a stereocontrolled electrophilic amination reaction of (S,S)-(+)-pseudoephedrine-based arylacetamide enolates with di-tertbutylazodicarboxylate. The arylglycines thus obtained turned out to be excellent chiral templates for the production of chiral, nonracemic 7,8-disubstituted 3-aryl-1,2,3,4-tetrahydroisoquinolines, through use of a synthetic sequence involving: (1) reduction of the arylglycines to the parent arylglycinols, (2) N-benzylation with appropriately substituted aromatic aldehydes and (3) Swern oxidation followed by acid catalysed cyclization of the obtained a-amino aldehydes.

Asymmetric synthesis of arylglycine amino acids using (S,S)-(+)- pseudoephedrine derived amides

Arylglycine aminoacids were obtained in good yields and with enantiomeric excesses higher than 99% by using an asymmetric amination reaction protocol on (S,S)-(+)-pseudoephedrine based arylacetamide enolates with di-tert-butylazodicarboxylate. Subsequent hydrazinolysis and hydrolysis yielded the target aminoacids.