250666-02-5

Usage

Uses

Used in Flavor and Fragrance Industry:
(S)alpha-amino-1,3-Benzodioxole-5-acetic acid is used as a key ingredient in the flavor and fragrance industry for its unique and appealing aroma, which can be described as minty or spicy.
Used in Pharmaceutical Synthesis:
(S)alpha-amino-1,3-Benzodioxole-5-acetic acid is utilized as a starting material or intermediate in the synthesis of various pharmaceuticals, contributing to the development of new drugs and medications.
Used in Agricultural Chemicals:
(S)alpha-amino-1,3-Benzodioxole-5-acetic acid is also employed in the production of agricultural chemicals, where it may serve as a component in the formulation of pesticides, herbicides, or other agrochemical products.
Used in Therapeutic Applications:
(S)alpha-amino-1,3-Benzodioxole-5-acetic acid has been studied for its potential therapeutic effects, including anti-inflammatory and analgesic properties, which could lead to its use in the development of treatments for various medical conditions.

Upstream product

• 250665-98-6 [2S,1'S,2'S]-(+)-2-amino-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 69810-87-3 amino-(3,4-methylenedioxyphenyl)-acetonitrile 
• 247118-52-1 (+)-<1'S,2'S>-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 250665-93-1 [2S,1'S,2'S]-(+)-2-[N,N'-bis(1,1-dimethylethoxycarbonyl)hydrazino]-N-(2'-hydroxy-1'-methyl-2'-phenylethyl)-N-methyl-2-(3,4-methylenedioxyphenyl)acetamide 
• 120-57-0 piperonal 

Downstream Products

• 73137-03-8 (6R,7R)-7-((S)-2-Amino-2-benzo[1,3]dioxol-5-yl-acetylamino)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 394740-13-7 (2S)-(-)-2-(2,3-dimethoxybenzyl)-N-methylamino-2-(3,4-methylenedioxyphenyl)ethanol 
• 394740-10-4 (2S)-(+)-2-(2,3-dimethoxybenzyl)amino-2-(3,4-methylenedioxyphenyl)ethanol 
• 394740-07-9 (2S)-(+)-(E)-2-(2,3-dimethoxybenzylideneamino)-2-(3,4-methylenedioxyphenyl)ethanol 
• 1026442-56-7 (S)-Benzo[1,3]dioxol-5-yl-[(2,3-dimethoxy-benzyl)-methyl-amino]-acetaldehyde 
• 394740-06-8 (2S)-(-)-2-amino-2-(3,4-methylenedioxyphenyl)ethanol 

Relevant academic research and scientific papers

Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides

Catalyzed by the nitrile hydratase and the amidease in Rhodococcus sp. AJ270 cells under very mild conditions, a number of α-aryl- and α-alkyl-substituted DL-glycine nitriles 1 rapidly underwent a highly enantioselective hydrolysis to afford D-(-)-α-amino acid amides 2 and L-(+)-α-amino acids 3 in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of a high L-enantioselective amidase and a low enantioselective nitrile hydratase. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of D-(-)-α-phenylglycine amide, biotransformation of DL-phenylglycine nitrile was applied in practical scale to produce both D- and L-phenylglycines in high optical purity.

Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles

Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

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.