184838-77-5

Usage

Uses

Used in Organic Synthesis:
3-Oxabicyclo[3.1.0]hexane-1-carboxylic acid, 2-oxo-, ethyl ester, (1R,5S)is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure and functional groups make it a useful component in the synthesis of complex organic molecules, including those with potential applications in material science and specialty chemicals.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-Oxabicyclo[3.1.0]hexane-1-carboxylic acid, 2-oxo-, ethyl ester, (1R,5S)is utilized as a key building block in the development of new drugs. Its specific stereochemistry and functional groups can be leveraged to create molecules with novel biological activities, potentially leading to the discovery of new therapeutic agents.
Used in Drug Development:
3-Oxabicyclo[3.1.0]hexane-1-carboxylic acid, 2-oxo-, ethyl ester, (1R,5S)is employed in drug development as a precursor for the synthesis of pharmaceutically active compounds. Its unique structural features and stereochemistry can be exploited to design molecules with improved pharmacokinetic and pharmacodynamic properties, enhancing their efficacy and safety in treating various diseases.
Used in Medicinal Chemistry:
In medicinal chemistry, 3-Oxabicyclo[3.1.0]hexane-1-carboxylic acid, 2-oxo-, ethyl ester, (1R,5S)is used as a versatile starting material for the synthesis of bioactive molecules. Its functional groups and stereochemistry can be manipulated to create compounds with specific binding affinities and selectivity for biological targets, contributing to the advancement of drug discovery efforts.

Upstream product

• 115314-14-2 (2s)-(+)-glycidyl 3-nitrobenzenesulfonate 
• 105-53-3 diethyl malonate 
• 15973-34-9 ethyl 2-propen-1-yl malonate 
• 1440528-09-5 1-allyl 3-ethyl 2-(diphenylsulfuranylidene)malonate 
• 67843-74-7 (S)-epichlorohydrin 
• 64-17-5 ethanol 
• 14208-48-1 ethyl 2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylate 

Downstream Products

• 1260148-52-4 C₃₀H₄₁IO₆Si 
• 1260148-66-0 C₃₀H₄₁IO₆Si 
• 1260148-54-6 C₃₀H₃₉IO₆Si 
• 1188474-84-1 3-benzoyl-1-[(1S,2S,5R)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]pyrimidine-2,4(1H,3H)-dione 
• 1188474-85-2 C₂₇H₃₀N₂O₃Si 
• 1188474-81-8 9-[(1S,2S,5R)-5-(tert-butyl-diphenylsilanyloxymethyl)bicyclo[3.1.0]hex-3-en-2-yl]-6-chloro-9H-purine 
• 1188474-82-9 C₂₈H₃₁N₅OSi 
• 577991-18-5 (1S,2R,5R)-5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-ol 
• 577991-20-9 1-[5-(tert-butyl-diphenyl-silanyloxymethyl)-bicyclo[3.1.0]hex-3-en-2-yl]-5-methyl-1H-pyrimidine-2,4-dione 
• 577991-19-6 (1'S,2'S,5'R)-1-{5-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]bicyclo[3.1.0]hex-3-en-2-yl}-5-methyl-3-(phenylcarbonyl)-1,3-dihydropyrimidine-2,4-dione 
• 1436505-18-8 methyl 5-(((1S,5S)-3-oxabicyclo[3.1.0]hexane-1-carboxamido)methyl)-2-chlorobenzoate 

Relevant academic research and scientific papers

Synthesis of enantiopure pseudo-L-vinylcyclopropyl nucleosides bearing quaternary carbon as potential anti-herpesvirus agent

Pseudo-l-vinylcyclopropyl adenine and guanine nucleosides 11 and 12 were designed and enantiopurely synthesized starting from (S)-epichlorohydrin using tandem alkylation, regioselective oxirane-ring opening, and chemoselective reduction as key steps. Copy

Discovery of benzo[d]imidazo[5,1-b]thiazole as a new class of phosphodiesterase 10A inhibitors

The design, synthesis and structure activity relationship studies of a series of compounds from benzo[d]imidazo[5,1-b]thiazole scaffold as phosphodiesterase 10A (PDE10A) inhibitors are discussed. Several potent analogs with heteroaromatic substitutions (9a-d) were identified. The anticipated binding mode of these analogs was confirmed by performing the in silico docking experiments. Later, the heteroaromatics were substituted with saturated heteroalkyl groups which provided a tool compound 9e with excellent PDE10A activity, PDE selectivity, CNS penetrability and with favorable pharmacokinetic profile in rats. Furthermore, the compound 9e was shown to be efficacious in the MK-801 induced psychosis model and in the CAR model of psychosis.

PRORENIN RECEPTOR LIGAND AND ANTAGONIST

PROBLEM TO BE SOLVED: To design and synthesize β strand mimetics using structural characteristics of cyclopropane and provide a new (pro)renin receptor ligand, and also provide a new (pro)renin receptor inhibitor that is excellent in solubility, stability

Dimeric TADDOL Phosphoramidites in Asymmetric Catalysis: Domino Deracemization and Cyclopropanation of Sulfonium Ylides

A gold-catalyzed asymmetric cyclopropanation of unactivated olefins with sulfonium ylides in the presence of a bimetallic catalyst with a novel dimeric TADDOL-phosphoramidite ligand is reported. This transformation allows a rare gold-catalyzed dynamic deracemization of chiral racemic substrates, where the same catalyst is responsible for several synergistic tasks in solution. The products are useful building blocks in synthesis and enable expeditious access to natural products.

Three-dimensional structural diversity-oriented peptidomimetics based on the cyclopropylic strain

Conformationally restricted peptidomimetics comprising eight stereoisomeric scaffolds with three-dimensional structural diversity were designed based on the structural features of cyclopropane, that is, cyclopropylic strain, which mimic wide-ranging tetra

SUBSTITUTED BICYCLIC HETEROARYL COMPOUNDS AS mPGES-1 INHIBITORS

The present invention relates to bicyclic compounds of formula (I) or pharmaceutically acceptable salt thereof as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (m PGES-1) enzyme and are therefore useful in the treatment of pain and/or inflammation from a variety of diseases or conditions, such as asthama, osteoarthritis, rheumatoid arthritis, acute or chronic pain and neurodegenerative diseases. (I)

PHTALAZINONE DERIVATIVES AS MPEGS -1 INHIBITORS

The present patent application is directed to bicyclic compounds of formula (I) or pharmaceutically acceptable salt thereof as mPGES-1 inhibitors. These compounds are inhibitors of the microsomal prostaglandin E synthase-1 (m PGES-1) enzyme and are theref

Synthesis of enantiomerically pure d- and l-bicyclo[3.1.0]hexenyl carbanucleosides and their antiviral evaluation

Based upon the fact that l-nucleosides have been generally known to be less cytotoxic than d-counterparts, l-bicyclo[3.1.0]hexenyl carbanucleoside derivatives with a fixed north conformation were designed and synthesized by employing a novel synthetic str

First synthesis of 2′-oxabicyclo[3.1.0]hexyl nucleosides with a north conformation

The first synthesis of 2′-oxabicyclo[3.1.0]hexyl nucleosides, a novel class of bicyclonucleosides, with a north conformation was successfully accomplished starting from (S)-epichlorohydrin via a tandem alkylation-lactonization, a less steric hindrance-dep

NOVEL METHOD FOR PREPARING PREGABALIN

The present invention relates to a method for preparing pregabalin ((S)-3-(aminomethyl)-5-methylhexanoic acid which is useful for the prevention and treatment of seizure disorders, pins, and psychiatric disorders. According to the present invention, pregabalin can be prepared in a high enantiomeric excess of 99% or more, without an additional step of separating or purifying its enantiomer.