88950-68-9

Usage

Uses

Used in Organic Synthesis:
(1R,2S)-1-(tert-butoxycarbonylamino)-2-phenylcyclopropanecarboxylic acid is utilized as a key building block in organic synthesis for the creation of intricate molecular structures. Its unique stereochemistry and functional groups enable the development of a wide range of complex organic compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (1R,2S)-1-(tert-butoxycarbonylamino)-2-phenylcyclopropanecarboxylic acid is employed as a precursor for the synthesis of potential drug candidates. The presence of the phenyl group introduces structural diversity and may contribute to the compound's biological activity, making it a valuable component in the design of new medications.
Used in Protective Group Chemistry:
The tert-butoxycarbonylamino group in (1R,2S)-1-(tert-butoxycarbonylamino)-2-phenylcyclopropanecarboxylic acid is used as a protective group for amine functional groups during organic synthesis. This allows chemists to carry out specific reactions without the amine group participating, thus preserving its reactivity for subsequent steps in the synthesis process.

Upstream product

• 88950-59-8 (3R,5R)-3-tert-Butoxycarbonylamino-5-phenyl-4,5-dihydro-3H-pyrazole-3-carboxylic acid 4-nitro-benzyl ester 
• 908094-04-2 phenyldiazomethane 
• 1479436-92-4 ethyl 1-amino-2-phenyl-cyclopropanecarboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 88950-54-3 N-(tert-butoxycarbonyl)-dehydroalanine p-nitrobenzyl ester 

Relevant academic research and scientific papers

Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: A novel class of irreversible inhibitors of histone demethylase KDM1A

Histone demethylase KDM1A (also known as LSD1) has become an attractive therapeutic target for the treatment of cancer as well as other disorders such as viral infections. We report on the synthesis of compounds derived from the expansion of tranylcypromine as a chemical scaffold for the design of novel demethylase inhibitors. These compounds, which are substituted on the cyclopropyl core moiety, were evaluated for their ability to inhibit KDM1A in vitro as well as to function in cells by modulating the expression of Gfi-1b, a well recognized KDM1A target gene. The molecules were all found to covalently inhibit KDM1A and to become increasingly selective against human monoamine oxidases MAO A and MAO B through the introduction of bulkier substituents on the cyclopropylamine ring. Structural and biochemical analysis of selected trans isomers showed that the two stereoisomers are endowed with similar inhibitory activities against KDM1A, but form different covalent adducts with the FAD co-enzyme.

Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ

A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ fro

A New Synthesis of Racemic Coronamic Acid and Other Cyclopropyl Amino Acids

A new method, in which various diazocompounds are added to a dehydro alanine derivative, allows the synthesis of coronamic acid and several other cyclopropyl amino acids.