54848-33-8

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-5-Oxotetrahydrofuran-2-carboxylic acid is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure and properties make it a valuable building block in the synthesis of various drugs, contributing to the creation of new and improved medications.
Used in Organic Chemistry:
(S)-(+)-5-Oxotetrahydrofuran-2-carboxylic acid is used as a synthetic intermediate in organic chemistry, allowing for the synthesis of a wide range of organic compounds. Its versatility in chemical reactions makes it an essential component in the development of new chemical entities and materials.
It is important to handle (S)-(+)-5-Oxotetrahydrofuran-2-carboxylic acid with care due to its potentially acidic and harmful nature.

Upstream product

• 21461-84-7 (2S)-tetrahydro-5-oxofuran-2-carboxylic acid 
• 53558-93-3 (R)-tetrahydro-5-oxo-2-furancarboxylic acid 
• 56-86-0 L-glutamic acid 
• 13095-48-2 L-hydroxyglutaric acid 
• 6893-26-1 D-Glutamic acid 

Downstream Products

• 1025893-00-8 -Tetrahydro-N-<5-(4-methoxyphenyl)-4-pentenyl>-5-oxo-2-furancarboxamide 
• 32780-06-6 (5S)-5-(hydroxymethyl)-2-oxo-tetrahydrofuran 
• 75629-74-2 (S)-(-)-Tetrahydro-5-oxo-2-furancarboxaldehyde 
• 183197-80-0 (S)-5-Oxo-tetrahydro-furan-2-carboxylic acid (3S,4R)-4-benzyloxy-tetrahydro-furan-3-yl ester 
• 183387-01-1 (S)-5-Oxo-tetrahydro-furan-2-carboxylic acid (3R,4S)-4-benzyloxy-tetrahydro-furan-3-yl ester 
• 325740-63-4 (S)-5-{(S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanoyl}-dihydro-furan-2-one 
• 625437-73-2 (S)-N-benzyl-5-oxotetrahydrofuran-2-carboxamide 
• 562817-52-1 (S)-N-(4-methoxybenzyl)-tetrahydro-5-oxo-2-furancarboxamide 
• 627077-40-1 (S)-5-[(2,4-Dimethoxy-3-methyl-phenyl)-dimethoxy-methyl]-dihydro-furan-2-one 
• 627077-41-2 (3R,5S)-5-[(2,4-Dimethoxy-3-methyl-phenyl)-dimethoxy-methyl]-3-methyl-dihydro-furan-2-one 
• 627077-42-3 (2S,4R)-1-(2,4-Dimethoxy-3-methyl-phenyl)-1,1-dimethoxy-4-methyl-hex-5-yn-2-ol 
• 1026622-66-1 Methanesulfonic acid (1S,3R)-1-[(2,4-dimethoxy-3-methyl-phenyl)-dimethoxy-methyl]-3-methyl-pent-4-ynyl ester 
• 91741-74-1 2-[({2-[(R)-1-((R)-2-{(R)-2-[((R)-1-tert-Butoxycarbonyl-pyrrolidine-2-carbonyl)-amino]-4-methyl-pentanoylamino}-3-methyl-butyrylamino)-3-cyano-propyl]-thiazole-4-carbonyl}-amino)-methyl]-thiazole-4-carboxylic acid pentafluorophenyl ester 
• 1263482-15-0 (S)-5-oxo-N-(3-(phenylsulfanyl)propyl)tetrahydrofuran-2-carboxamide 

Relevant academic research and scientific papers

Enantioselective synthesis of δ-ketobutanolides from (L)-glutamic acid via organomanganese reagents

Various optically active δ-ketobutanolides were easily prepared in good yields, with an excellent enantiomeric purity, by acylation of organomanganese reagents with the butyrolactone acid chloride 3 prepared from natural (L)-glutamic acid. The reaction takes place in THF under mild conditions (-10°C, 3h or 3% CuCl, -30°C, 20 min.).

Stereoisomeric flavour compounds. LXIII. 4-Hydroxypentan-2-one enantiomers - Structure and properties

From racemic 4-hydroxypentan-2-one and (S)-tetrahydro-5-oxo-2-furancarboxylic acid chloride the corresponding diastereomeric esters were generated, subsequently separated by liquid chromatography and hydrolyzed to yield pure enantiomers of 4-hydroxypentan-2-one. The X-ray crystal structures of the diastereomeric esters as well as the odour impression of the pure 1,3-ketol enantiomers are reported.

Synthesis of four diastereomers of sclerophytin F and structural reassignment of several sclerophytin natural products

Synthesis of the triol that has been proposed to be the marine natural product sclerophytin F has been completed along with the syntheses of three diastereomers. Comparison of the NMR spectroscopic data for all four compounds to the data reported for the natural product reveals that sclerophytin F is not the 3S diastereomer of sclerophytin A as proposed by Friedrich and Paquette. Re-analysis of the NMR spectroscopic data for known sclerophytin natural products and synthetic analogues leads to the conclusion that sclerophytins E and F are the same compound. This finding has allowed structural reassignment of several other cladiellin natural products.

Stereocontrolled Synthesis of 2,5-Linked Monotetrahydrofuran Units of Acetogenins

An approach to the stereocontrolled monotetrahydrofuran units of acetogenins is described.The NMR data of the two synthesized diastereoisomers 11 and 12 allow us to define the relative configuration of the monotetrahydrofuran acetogenins.

Stereoselective synthesis of zooxanthellactone

The marine polyunsaturated natural product zooxanthellactone was synthesized in six steps and in 11% overall yield from eicosapentaenoic acid. The key synthetic steps were a Sonogashira cross-coupling reaction and a stereoselective semi-reduction. These efforts, together with NMR and optical rotation data, confirmed the reported structure of zooxanthellactone.

Construction the a-b bicyclic ring structure of stemocurtisine

In this paper, the synthesis of the A-B bicyclic ring structure 3 of the natural product Stemocurtisine is described. The synthesis was accomplished in seven synthetic steps from com-mercially available L-glutamic acid. The key step involved a borono-Mannich reaction between the hemiaminal 6 and trans-β-styryl boronic acid and trans-β-styrylpotassiumtrifluoroborate to prepare the cis diene 4. Attempts to prepare the A-B-C ring compound 2 via intramolecular epox-ide ring opening followed by rearrangement under different basic conditions were unsuccessful. The only unreactive starting material was recovered.

NOVEL SUBSTITUTED AMINOTHIAZOLOPYRIMIDINEDIONE FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION

The present invention relates to compounds of formula (I), wherein R1 to R4 are as described herein, and their pharmaceutically acceptable salts, enantiomers or diastereomers thereof, and compositions including the compounds for use

NOVEL 3-SUBSTITUTED 5-AMINO-6H-THIAZOLO[4,5-D]PYRIMIDINE-2,7-DIONE COMPOUNDS FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION

The present invention relates to compounds of formula (I), wherein R1, R2 and R3 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

NOVEL SUBSTITUTED AMINOTHIAZOLOPYRIMIDINEDIONE FOR THE TREATMENT AND PROPHYLAXIS OF VIRUS INFECTION

The present invention relates to compounds of formula (I), wherein R1 to R5 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

Enantiopure chelating agents for chelator coupled pharmaceuticals, corresponding preparation method thereof and chelator coupled pharmaceuticals

According to the present invention an enantiopure chelating compound of general Formula 10A or 10B is provided: wherein each of R1 through R3 is independently selected hydrogen, substituted or unsubstituted C1-C20 alkyl, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C3-C10 cycloalkyl, substituted or unsubstituted C6-C60 aryl, or -Si(R4)(R5)(R6), and each of R4 through R6 is independently selected a substituted or unsubstituted group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, C1-C20 alkoxy, C3-C10 cycloalkyl, C6-C60 aryl, and C6-C60 aryloxy. The present invention further refers to a corresponding preparation method of the chelating compound and chelator coupled pharmaceuticals including the same.