139683-93-5

Basic information

• Product Name: (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL
• Synonyms: (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL
• CAS NO: 139683-93-5
• Molecular Formula: C6H9NO2
• Molecular Weight: 127.14
• Mol File: 139683-93-5.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL(139683-93-5)
• EPA Substance Registry System: (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL(139683-93-5)

Safety Data

• Hazardous Substances Data: 139683-93-5(Hazardous Substances Data)

Usage

Description

(R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL, also known as (R)-2-Amino-1-(2-furyl)ethanol, is a chiral molecule characterized by a furan ring and an amino group attached to a chiral center. (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL is recognized for its stereochemical properties, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and chiral ligands.

Uses

Used in Pharmaceutical Industry:
(R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL is used as a building block for the synthesis of chiral drugs, leveraging its unique stereochemistry to create enantiomerically pure pharmaceuticals. This application is crucial for ensuring the efficacy and safety of drugs, as different enantiomers can have distinct biological activities.
Used in Chemical Industry:
In the chemical industry, (R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL is used as a precursor for the production of fine chemicals. Its structural features allow for the creation of a variety of complex molecules with specific properties, contributing to the development of new materials and compounds.
Used in Asymmetric Catalysis:
(R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL is utilized as a ligand in asymmetric catalysis, a process that is essential for the production of optically active compounds. As a chiral ligand, it helps to control the stereochemistry of reactions, enabling the selective synthesis of desired enantiomers.
Used in Synthesis of Chiral Auxiliaries and Ligands:
(R)-2-AMINO-1-(FURAN-2-YL)-ETHANOL is also used in the synthesis of chiral auxiliaries and ligands for organic synthesis. These auxiliary and ligand molecules are vital for controlling the stereochemistry of various chemical reactions, leading to the production of enantiomerically enriched products.

Upstream product

• 1007402-77-8 (R)-[2-azido-1-(furan-2-yl)ethoxy](tert-bityl)dimethylsilane 
• 98-01-1 furfural 
• 121986-08-1 (R)-(-)-2-(2-furyl)-2-hydroxyacetonitrile 
• 118299-63-1 2-azido-1-(furan-2-yl)-ethanone 
• 15109-94-1 1-(2-furyl)-2-bromoethanone 
• 1192-62-7 1-(2-furyl)-1-ethanone 

Downstream Products

• 804511-81-7 N-(4-chlorobenzyl)-2-((((2R)-2-(2-furyl)-2-hydroxyethyl)(methyl)amino)methyl)-4-oxo-7-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide 
• 804511-38-4 N-(4-chlorobenzyl)-2-((((2R)-2-(2-furyl)-2-hydroxyethyl)(methyl)amino)methyl)-4-oxo-7-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide 
• 804511-32-8 N-(4-chlorobenzyl)-7-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-2-((((2R)-2-(2-furyl)-2-hydroxyethyl)(methyl)amino)methyl)-4-oxo-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide 
• 804511-93-1 N-(4-chlorobenzyl)-2-((((2R)-2-(2-furyl)-2-hydroxyethyl)(methyl)amino)methyl)-4-oxo-7-(2-(2-(tetrahydro-2H-pyran-2-yloxy)ethoxy)ethyl)-4,7-dihydrothieno[2,3-b]pyridine-5-carboxamide 

Relevant articles and documents

One-pot combination of enzyme and Pd nanoparticle catalysis for the synthesis of enantiomerically pure 1,2-amino alcohols

One-pot combinations of sequential catalytic reactions can offer practical and ecological advantages over classical multi-step synthesis schemes. In this context, the integration of enzymatic and chemo-catalytic transformations holds particular potential for efficient and selective reaction sequences that would not be possible using either method alone. Here, we report the one-pot combination of alcohol dehydrogenase-catalysed asymmetric reduction of 2-azido ketones and Pd nanoparticle-catalysed hydrogenation of the resulting azido alcohols, which gives access to both enantiomers of aromatic 1,2-amino alcohols in high yields and excellent optical purity (ee >99%). Furthermore, we demonstrate the incorporation of an upstream azidolysis and a downstream acylation step into the one-pot system, thus establishing a highly integrated synthesis of the antiviral natural product (S)-tembamide in 73% yield (ee >99%) over 4 steps. Avoiding the purification and isolation of intermediates in this synthetic sequence leads to an unprecedentedly low ecological footprint, as quantified by the E-factor and solvent demand.

Large-scale synthesis of (R)-2-amino-1-(2-furyl)ethanol via a chemoenzymatic approach

A two-step chemoenzymatic synthesis of (R)-2-amino-1-(2-furyl)ethanol for laboratory production was developed followed by successful up-scaling to kilogram scale. The generation of the asymmetric centre was accomplished by a highly enantioselective cyanohydrin reaction of furan-2-carbaldehyde with hydrocyanic acid catalyzed by the hydroxynitrile lyase from Hevea brasiliensis. Subsequent sodium borohydride reduction furnished the desired product with an enantiomeric excess of higher than 99.5%. This procedure can be considered a convenient general route for the stereoselective synthesis of ethanol amine derivatives underlining the role of biocatalysis for the generation of stereogenic centres in the synthesis of chiral intermediates.