889461-57-8

Basic information

• Product Name: (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate
• Synonyms: (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate;(1S,2S)-1,2-DIETHYL-CYCLOPROPANE-1,2-DICARBOXYLIC ACID
• CAS NO: 889461-57-8
• Molecular Formula: C9H14O4
• Molecular Weight: 186.20506
• Mol File: 889461-57-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• CAS DataBase Reference: (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate(889461-57-8)
• EPA Substance Registry System: (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate(889461-57-8)

Safety Data

• Hazardous Substances Data: 889461-57-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate is used as an intermediate in the synthesis of (O846925), a compound with potential therapeutic applications.
Used in Enzyme Inhibitor Synthesis:
In the field of biochemistry, (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate is utilized as a precursor in the synthesis of aza-peptidyl inhibitors of lysosomal asparaginyl endopeptidase, also known as legumain. These inhibitors play a crucial role in studying the function and regulation of legumain, an enzyme implicated in various physiological and pathological processes.
Used in Cancer Research:
(1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate is also employed in the synthesis of irreversible epidermal growth factor receptor (EGFR) inhibitors. EGFR is a receptor tyrosine kinase involved in cell growth and division, and its dysregulation is associated with various cancers. Inhibitors targeting EGFR can potentially be used in cancer therapy to block the growth and proliferation of cancer cells.
Used in Protease Research:
Furthermore, (1S,2S)-Diethyl cyclopropane-1,2-dicarboxylate is used in the development of probes for cathepsins, a group of protease enzymes that play a significant role in various biological processes, including antigen presentation, apoptosis, and tissue remodeling. Understanding and targeting cathepsins can provide insights into the treatment of various diseases, including cancer and neurodegenerative disorders.

Upstream product

• 3999-55-1 diethyl trans-cyclopropane-1,2-dicarboxylate 
• 64-17-5 ethanol 
• 14590-54-6 (1S,2S)-cyclopropane-1,2-dicarboxylic acid 
• 623-73-4 diazoacetic acid ethyl ester 
• 140-88-5 ethyl acrylate 

Downstream Products

• 53187-82-9 (trans-cyclopropane-1,2-diyl)dimethanol 
• 14590-54-6 (1S,2S)-cyclopropane-1,2-dicarboxylic acid 

Relevant articles and documents

T-TYPE CALCIUM CHANNEL BLOCKER

To provide a novel T-type calcium channel blocker. A compound represented by the following General Formula (I), a tautomer or a stereoisomer of the compound, a pharmaceutically acceptable salt of the compound, or a solvate of the compound, the tautomer, the stereoisomer, or the salt is used as a T-type calcium channel blocker. wherein A represents a phenyl which may have a substituent, a 4-membered to 6-membered heteroaryl ring composed of one to three identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom and carbon atoms as ring-constituting atoms, or a heterocondensed ring composed of the heteroaryl ring and either a benzene ring or a 6-membered heteroaryl ring composed of one to two nitrogen atoms and carbon atoms, wherein the heteroaryl ring or the heterocondensed ring may have a substituent and is bonded to a nitrogen atom of the adjacent cyclic amino by means of a carbon atom constituting these rings; B represents a phenyl which may have a substituent, a 5-membered or 6-membered heteroaryl ring composed of one to three identical or different heteroatoms selected from an oxygen atom, a sulfur atom, and a nitrogen atom and carbon atoms as ring-constituting atoms, or a heterocondensed ring composed of the heteroaryl ring and either a benzene ring or a 6-membered heteroaryl ring composed of one to two nitrogen atoms and carbon atoms, wherein the heteroaryl ring or the heterocondensed ring may have a substituent and is bonded to the adjacent cyclopropyl ring by means of a carbon atom constituting these rings; R1 and R2, which may be identical or different, each represent a hydrogen atom, a halogen atom, or the like; R3 represents a hydrogen atom, a halogen atom, or the like; n and m, which may be identical or different, each represent 0 or 1; and p represents 1 or 2.

Highly stereoselective cyclopropanation of α,β-unsaturated carbonyl compounds with methyl (diazoacetoxy)acetate catalyzed by a chiral ruthenium(II) complex

Tantalizing triangles: The title reaction gives bicarbonyl cyclopropane products that can lead to versatile intermediates with high yields and stereoselectivities. This system was also applied to the enantioselective total synthesis of spiro cyclopropane oxindole, an HIV-1 nonnucleoside reverse transcriptase inhibitor. Copyright

ASYMMETRIC CYCLOPROPANATION OF ELECTRON-DEFICIENT OLEFINS WITH DIAZO REAGENTS

Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins.

A convenient chemo-enzymatic synthesis and 18F-labelling of both enantiomers of trans-1-toluenesulfonyloxymethyl-2-fluoromethyl-cyclopropane

The present report is concerned with a stereoselective, reliable route to trans-1,2-disubstituted cyclopropanes and in particular to (S,S)-1- tosyloxymethyl-2-fluoromethyl-cyclopropane (1) and (R,R)-1-tosyloxymethyl-2- fluoromethyl-cyclopropane (ent-1) as conformationally restricted, terminally fluorinated C4-building blocks for medicinal chemistry. The enzymatic kinetic resolution based synthesis of 1 and ent-1 utilises inexpensive, commercially available starting materials. It is based on enantiomeric resolution of rac-cyclopropane carboxylic esters using esterase from Streptomyces diastatochromogenes. Both enantiomers of 1 were prepared selectively in high overall yield over nine steps, starting from ethyl acrylate. The successful radiosynthesis of [18F]-1 and [18F]-ent-1 is also reported.

Cobalt-catalyzed asymmetric cyclopropanation of electron-deficient olefins

The cobalt(II) complex of a D2-symmetric chiral porphyrin [Co(1)] is an effective catalyst for asymmetric cyclopropanation of electron-deficient olefins, including α,β-unsaturated esters, amides, ketones, and nitriles. Due to the absence of dimerization of diazo compounds, the catalytic reactions can be performed in one-pot protocol using olefins as the limiting reagent, forming the desired electrophilic cyclopropane derivatives in high yields and selectivities under mild conditions. In most cases, both excellent diastereo- and enantioselectivity were achieved. Copyright