19684-04-9

Usage

Uses

Used in Organic Synthesis:
(R)-methyl 5-oxotetrahydrofuran-2-carboxylate is used as a reagent in organic synthesis for the preparation of various pharmaceuticals and fine chemicals. Its unique structure and reactivity make it a valuable component in the development of new and innovative compounds.
Used in Pharmaceutical Industry:
(R)-methyl 5-oxotetrahydrofuran-2-carboxylate is used as a key intermediate in the synthesis of pharmaceuticals. Its ability to form a wide range of derivatives with different properties allows for the creation of new drugs with improved efficacy and reduced side effects.
Used in Flavor and Fragrance Industry:
(R)-methyl 5-oxotetrahydrofuran-2-carboxylate is used as a building block in the manufacture of flavors and fragrances. Its unique chemical properties contribute to the development of novel and complex scents, enhancing the sensory experience of various products.
Used in the Synthesis of Biologically Active Compounds:
(R)-methyl 5-oxotetrahydrofuran-2-carboxylate is used as a versatile building block for the synthesis of biologically active compounds. Its ability to undergo various chemical transformations allows for the creation of a diverse range of derivatives with potential applications in medicine, agriculture, and other fields.

Upstream product

• 13192-04-6 dimethyl 2-ketoglutarate 
• 67-56-1 methanol 
• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 

Downstream Products

• 155768-48-2 -Methyl 2-hydroxy-5-<<5-(4-methoxyphenyl)-4-pentenyl>amino>-5-oxopentanoate 

Relevant academic research and scientific papers

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.

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.

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.