54848-33-8

Basic information

• Product Name: (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
• Synonyms: (S)-(+)-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID;(S)-(+)-5-OXO-2-TETRAHYDROFUROIC ACID;(S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID;(S)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID;(S)-(+)-TETRAHYDRO-5-OXO-2-FURANCARBOXYLIC ACID;(S)-(+)-TETRAHYDRO-5-OXO-2-FURANECARBOXYLIC ACID;(S)-(+)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE;(S)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE
• CAS NO: 54848-33-8
• Molecular Formula: C₅H₅ClO₃
• Molecular Weight: 130.1
• Product Categories: ACIDHALIDE
• Mol File: 54848-33-8.mol
• Article Data: 38

Chemical Properties

• Melting Point: 71-73 °C(lit.)
• Boiling Point: 150-155 °C0.2 mm Hg(lit.)
• Appearance: /
• CAS DataBase Reference: (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID(54848-33-8)
• EPA Substance Registry System: (S)-(+)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID(54848-33-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 54848-33-8(Hazardous Substances Data)

Usage

General Description

"(S)-(+)-5-Oxotetrahydrofuran-2-carboxylic acid" is a chemical compound that belongs to the class of heterocyclic carboxylic acids and derivatives. Its molecular formula is C5H6O4, and it has a molar mass of 130.10 grams per mole. It has a chiral center, which results in its specific name, (S)-(+), indicating the configuration of its atoms in three-dimensional space. Being an organic compound, this acid is commonly utilized as a synthetic intermediate in organic chemistry, particularly in pharmaceuticals. However, details about its specific applications are not widely documented. It should be handled with care due to its potentially acidic and harmful nature.

Upstream product

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

Downstream Products

• 75989-44-5 (S)-5-(1'-oxo-2'-phenylethyl)dihydrofuran-2(3H)-one 
• 325740-63-4 (S)-5-{(S)-3-[4-Methoxy-3-(3-methoxy-propoxy)-benzyl]-4-methyl-pentanoyl}-dihydro-furan-2-one 
• 902131-96-8 C₁₇H₂₄O₄ 
• 902131-97-9 C₁₇H₂₆O₄ 
• 902131-98-0 C₂₀H₃₀O₃ 
• 902132-00-7 C₁₉H₂₈O₄ 
• 902132-02-9 C₂₂H₃₄O₄ 
• 902132-03-0 C₂₈H₄₈O₄Si 
• 562817-53-2 (3S)-1-(4-methoxybenzyl)-3-hydroxypiperidine-2,6-dione 
• 562817-54-3 (S)-3-[(tert-butyldiphenylsilyl)oxy]-1-(4-methoxybenzyl)-2,6-piperidinedione 
• 125225-51-6 (5S,1'R)-5-(1'-hydroxy-2'-phenylethyl)dihydrofuran-2(3H)-one 
• 125225-52-7 (5S,1'S)-5-(1'-hydroxy-2'-phenylethyl)dihydrofuran-2(3H)-one 
• 145761-24-6 (5S,1'S)-5-(1'-methanesulfonyloxy-2'-phenylethyl)dihydrofuran-2(3H)-one 
• 133333-27-4 tert-butyl (1S)-1-[(2S)-5-oxotetrahydrofuran-2-yl]-2-phenylethylcarbamate 

Relevant articles and documents

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.).

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.

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.

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 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.