21461-85-8

Usage

Uses

Used in Organic Synthesis:
(S)-methyl 5-oxotetrahydrofuran-2-carboxylate is used as a building block in the synthesis of various pharmaceuticals and natural products. Its unique structure and reactivity make it a valuable component in creating complex organic molecules.
Used in Pharmaceutical Research and Development:
As a chiral molecule with potential biological activities, (S)-methyl 5-oxotetrahydrofuran-2-carboxylate is used in pharmaceutical research and development. It is studied for its potential as a drug candidate, offering new avenues for the treatment of various diseases and conditions.
Used in Analytical Chemistry:
(S)-methyl 5-oxotetrahydrofuran-2-carboxylate is used as a reference standard in analytical chemistry. It aids in the identification and quantification of similar compounds in a range of samples, ensuring accurate and reliable results in chemical analysis.

Upstream product

• 13192-04-6 dimethyl 2-ketoglutarate 
• 3885-29-8 (+/-)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester 
• 67-56-1 methanol 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 56-86-0 L-glutamic acid 
• 81077-10-3 methyl 2-hydroxy-4-(metoxycarbonyl)butanoate 
• 328-50-7 α-ketoglutaric acid 
• 186581-53-3 diazomethane 

Downstream Products

• 1126-51-8 (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester 
• 239125-39-4 5-methyl (3S,5S)-3-acetylamino-2-oxotetrahydrofuran-5-carboxylate 
• 239125-39-4 5-methyl (3R,5S)-3-acetylamino-2-oxotetrahydrofuran-5-carboxylate 

Relevant academic research and scientific papers

A new synthesis of alkaloid (S)-3-hydroxypiperidin-2-one and its O-TBS protected derivative

(Chemical Equation Presented) From the known lactone (S)-4, easily derived from L-glutamic acid, a scalable approach to chiral building block O-silylated 3-hydroxypiperidin-2-one 3 and alkaloid 1 was achieved in five and six-steps respectively. The key st

Synthesis of spirolactones by 1,3-dipolar cycloadditions to methyl (S)-3-[(E)-cyanomethylidene]-2-oxotetrahydrofuran-5-carboxylate

Treatment of methyl (S)-5-[(E)-(dimethylamino)methylidene]-2-oxotetrahydrofuran-5-carboxylate (2) with potassium cyanide in acetic acid gave (S)-5-[(E)-cyanomethylidene]-2-oxotetrahydrofuran-5-carboxylate (3), which was used as chiral dipolarophile in 1,3-dipolar cycloadditions. Reactions of 3 with diazomethane (4) and nitrile oxides 5a-c afforded spirolactones 6-8 in 24-34% diastereomeric excess, while with diazomethane (4) in the presence of triethylamine, methyl 3-cyanomethyl-2-methoxyfuran-5carboxylate (12) was obtained.

MODULATORS OF G-PROTEIN COUPLED RECEPTORS

This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt and/or hydrate and/or prodrug of the compound) that modulate (e.g., agonize or partially agonize or antagonize) glucagon?like peptide?1 receptor ("GLP?1R") and/or the gastric inhibitory polypeptide receptor ("GIPR"). The chemical entities are useful, e.g., for treating a subject (e.g., a human) having a disease, disorder, or condition in which modulation (e.g., agonism, partial agonism or antagonism) of GLP?1R and/or GIPR activities is benficial for the treatment or prevention of the underlying pathology and/or symptoms and/or progression of the disease, disorder, or condition. In some embodiments, the modulation results in an enhancment of (e.g., an increase in) existing levels (e.g., normal or below normal levels) of GLP?1R and/or GIPR activity (e.g., signaling). In some embodiments, the chemical entities described herein further modulate (e.g., attenuate, uncouple) -arrestin signaling relative to what is observed with the native ligand. This disclosure also features compositions as well as other methods of using and making the said chemical entities.

Development of a multigram asymmetric synthesis of 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester, (R)-tert-Bu4-DOTAGA1

A process for the multigram asymmetric synthesis of the chiral tetraazamacrocycle 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl- 1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester ((R)-tert-Bu4-DOTAGA, 4) has been devised and demonstrated. The nine-step synthesis features an improved synthesis of 2-(S)-5- oxotetrahydrofuran- 2-carboxylic acid, tert-butyl ester 8, the precursor to the novel alkylating agent (S)-5-benzyl 1-tert-butyl 2-(methylsulfonyloxy) pentanedioate 12, which was used to introduce an orthogonally protected chiral glutarate arm to the 1,4,7,10-tetraazacyclododecane (cyclen) nucleus in high optical purity. Cyclen derivative (R)-t-Bu4-DOTAGA, 4, a key intermediate for the manufacture of a magnetic resonance imaging (MRI) candidate, was produced with high chemical (≥95%) and optical (ee ≥ 97%) purity. The process developed was successfully applied to the kilogram-scale cGMP synthesis of (R)-t-Bu4-DOTAGA.

Combination strategy using pure enzymes and whole cells as biocatalysts for the preparation of 2-hydroxyesters and lactones from 2-oxoglutaric acid

An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarate from 2-oxoglutaric acid. An innovative combination strategy that uses pure enzymes and whole microbial cells in the same process was used to prepare enantiomerically pure 3-carboxyalkyl-γ-butyrolactones and several alkyl esters of 2-hydroxyglutarates from 2-oxoglutaric acid. The method involves two consecutive biocatalytic steps. The first step, which converts the 2-oxoglutaric acid into the corresponding dialkyl esters, was catalyzed by a lipase. Then in the second step, by microbial reduction of the dialkyl-2-oxoglutarates, it is possible to obtain 3-carboxyalkyl-γ- butyrolactones or 2-hydroxyesters depending on the length of the chain in the alkyl moiety of the esters and on the fresh or lyophilized status of the cells.

A direct method for the conversion of terminal epoxides into γ-butanolides

A new and efficient process for the conversion of terminal epoxides to γ-butanolides is described involving Lewis acid promoted epoxide ring-opening by 1-morpholino-2-trimethylsilyl acetylene. Addition of a terminal epoxide to a solution of the ynamine an

Asymmetric synthesis of alkyl 5-oxotetrahydrofuran-2-carboxylates by enantioselective hydrogenation of dialkyl 2-oxoglutarates over cinchona modified Pt/Al2O3 catalysts

The first direct asymmetric synthesis of chiral alkyl 5- oxotetrahydrofuran-2-carboxylates (up to 96% ee), which are important building blocks in the synthesis of natural products by heterogeneous cinchona-modified Pt-catalyzed hydrogenation of α-ketoglutaric acid esters and subsequent cyclization of hydroxy esters is described.

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters from dialkyl 2-oxoglutarates

Enantiomerically pure tetrahydro-5-oxo-2-furancarboxylic esters can be prepared either by enzymatic resolution of the racemic γ-lactones themselves or by bioreduction with baker's yeast of dialkyl 2-oxoglutarates and subsequent cyclization of the resulting dialkyl 2-hydroxyglutarates. The best results were obtained by the former route, by which the desired compounds were isolated in high enantiomeric excess. Bioreductions were less satisfactory. In fact the hydroxyester intermediates were initially formed as racemic mixtures and their final enantiomeric enrichment was reached by asymmetric destruction, occurring in the bioreaction medium, however at the same time large amounts of alkyl 4-hydroxybutanoates were formed as side products.

NAD(P)+-NAD(P)H Models. 59. 1,2- Versus 1,4-Reduction of β,γ-Unsaturated α-Keto Ester

Depending on the reactivity of the reducing agent, β,γ-unsaturated α-keto ester is reduced into either β,γ-unsaturated α-hydroxy ester or saturated α-keto ester as the result of 1,2- or 1,4-reduction.

SYNTHESIS OF D-AMICETOSE AND L-RHODINOSE FROM L-GLUTAMIC ACID

L-Glutamic acid has been converted into a separable mixture of D-amicetono- and L-rhodinono-γ-lactones by a sequence involving transformation into (S)-γ-carboxy-γ-butyrolactone (2), conversion of 2 into the corresponding methyl ketone by the diazoketone route, and selective reduction with zinc borohydride or boranemethyl sulfide.Reduction of the two lactones with di-isobutylaluminium hydride gave the corresponding deoxy sugars.In spite of some improvements in the preparation of 2, the optical yield of this step was only ca. 80percent, but one crystallisation from chloroform raised the optical purity to 96percent.The subsequent steps produced a loss in optical purity of only 4percent.