31420-52-7

Usage

Uses

Used in Organic Synthesis:
(1R,2S)-rel-1,2-Cyclobutanedicarboxylic acid, 1-Methyl ester is used as a building block in organic synthesis for creating more complex molecules. Its unique structure and reactivity make it a valuable component in the synthesis of various organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, (1R,2S)-rel-1,2-Cyclobutanedicarboxylic acid, 1-Methyl ester is utilized as a key intermediate in the development of new drugs. Its specific stereochemistry and functional groups contribute to the design and synthesis of pharmaceutically relevant molecules.
Used in Polymer Science:
(1R,2S)-rel-1,2-Cyclobutanedicarboxylic acid, 1-Methyl ester has potential applications in the field of polymer science. Its properties can be exploited to design and synthesize novel polymers with specific characteristics, such as improved mechanical strength, thermal stability, or biocompatibility.
Used as a Catalyst in Chemical Reactions:
Due to its reactivity and functional groups, (1R,2S)-rel-1,2-Cyclobutanedicarboxylic acid, 1-Methyl ester can also serve as a catalyst in various chemical reactions. Its ability to facilitate specific transformations can enhance the efficiency and selectivity of these processes.

InChI:InChI=1/C7H10O4/c1-11-7(10)5-3-2-4(5)6(8)9/h4-5H,2-3H2,1H3,(H,8,9)

Upstream product

• 67-56-1 methanol 
• 4462-96-8 3-oxabicyclo[3.2.0]heptane-2,4-dione 
• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 

Downstream Products

• 7687-30-1 butyl cis-2-(tosyloxymethyl)cyclobutanecarboxylate 
• 84673-48-3 methyl trans-2-(cyanomethyl)cyclobutanecarboxylate 

Relevant academic research and scientific papers

INHIBITORS OF DIACYLGLYCEROL O-ACYLTRANSFERASE TYPE 1 ENZYME

The present invention relates to compounds of formula (I) wherein R1, R3, X, Q, Z, A, D, m, and n are defined herein. Pharmaceutical compositions and methods for treating DGAT-1 related diseases or conditions are also disclosed.

Synthesis of the constrained glutamate analogues (2S,1′R,2′R)- and (2S,1′S,2′S)-2-(2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I by enzymatic transamination

Optically pure trans-cyclobutane analogues of glutamic acid are prepared by highly selective enzymatic transamination of a single racemic trans-cyclobutane α-ketoglutaric acid derivative 5, which is synthesized in five steps from maleic anhydride. (2S,1′R,2′R)- and (2S,1′S,2′S)-2- (2′-carboxycyclobutyl)glycines L-CBG-II and L-CBG-I are obtained using aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT), respectively.

Stereoselective chemoenzymatic synthesis of the four stereoisomers of L-2-(2-carboxycyclobutyl)glycine and pharmacological characterization at human excitatory amino acid transporter subtypes 1, 2, and 3

The four stereoisomers of L-2-(2-carboxycyclobutyl)glycine, L-CBG-I, L-CBG-II, L-CBG-III, and L-CBG-IV, were synthesized in good yield and high enantiomeric excess, from the corresponding cis and trans-2- oxalylcyclobutanecarboxylic acids 5 and 6 using the enzymes aspartate aminotransferase (AAT) and branched chain aminotransferase (BCAT) from Escherichia coli. The four stereoisomeric compounds were evaluated as potential ligands for the human excitatory amino acid transporters, subtypes 1, 2, and 3 (EAAT1, EAAT2, and EAAT3) in the FLIPR membrane potential assay. While the one trans-stereoisomer, L-CBG-I, displayed weak substrate activity at all three transporters, EAAT1-3, we found a particular pharmacological profile for the other trans-stereoisomer, L-CBG-II, which displayed EAAT1 substrate activity and inhibitory activity at EAAT2 and EAAT3. Whereas L-CBG-III was found to be a weak inhibitor at all three EAAT subtypes, the other cis-stereoisomer L-CBG-IV was a moderately potent inhibitor with 20-30-fold preference for EAAT2/3 over EAAT1.

Enantioselective synthetic approaches to cyclopropane and cyclobutane β-amino acids: Synthesis and structural study of a conformationally constrained β-dipeptide

Synthetic approaches to carbocyclic compounds, namely cyclopropane and cyclobutane β-amino acids, are presented. One of them is based on enzymatic desymmetrization of meso diesters, leading to the enantioselective production of cis-hemiesters, which afforded β-amino acids through Curtius rearrangements. The enantiomeric excess for the cyclobutane derivatives was 91% whereas the cyclopropanes were obtained in 63% ee. According to another strategy, an enantiomerically pure cyclopropane trans-β-amino acid, bearing a quaternary center, has been synthesized from a homochiral precursor easily available from D-glyceraldehyde. The preparation and structural investigation of the first synthesized cyclobutane containing dipeptide is also described. A hairpin-like conformation of this molecule in the solid state has been demonstrated by X-ray structural analysis, showing crystal packing induced by the presence of the rigid cyclobutane moiety and the formation of intermolecular hydrogen bonds. NMR experiments confirmed that these molecules also tend to produce aggregates in solution. On the contrary, theoretical calculations suggest that intramolecular interactions are important in the gas phase, as expected. Copyright (C) 2000 Elsevier Science Ltd.

Stereoselective synthesis of (-)-(1R,2S)-2-aminocyclobutane-1-carboxylic acid, a conformationally constrained β-amino acid

The title compound as well as some derivatives have been synthesized for the first time in optically active form by means of a chemoenzymatic transformation used to induce asymmetry in achiral precursors. The enantio- and diastereomeric purity has been determined by HPLC and NMR techniques.