31420-60-7

Usage

Uses

Used in Organic Synthesis:
(cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester is used as a building block for the synthesis of various organic compounds, contributing to the structural diversity and functional groups required in the final products.
Used in Organic Chemistry as a Reagent:
In the field of organic chemistry, (cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester serves as a reagent, facilitating specific chemical reactions and transformations that are essential for the development of new molecules and materials.
Used in Pharmaceutical Industry:
(cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester may be utilized in the pharmaceutical industry for the development of new drugs, given its potential to be a part of complex molecular structures with therapeutic properties.
Used in Chemical Research:
(cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester is also valuable in chemical research, where it can be employed to study reaction mechanisms, explore new synthetic pathways, and understand the properties of novel chemical entities.
Safety and Handling:
It is important to handle (cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester with care due to its potential harmful effects if ingested, inhaled, or comes into contact with the skin or eyes. It is advisable to store and handle (cis)-(1RS,2SR)-cyclobutane-1,2-dicarboxylic acid monomethyl ester in a well-ventilated area and to use appropriate personal protective equipment when working with it.

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

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.

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.

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.