5-Oxo-tetrahydro-furan-2-carboxylic, CAS No. 53558-93-3

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53558-93-3

Catalog No. EBD24076

CAS 53558-93-3

Name 5-Oxo-tetrahydro-furan-2-carboxylic

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Basic Information

Synonyms: (2R)-5-oxotetrahydrofuran-2-carboxylate (R)-5-Oxotetrahydro-2-furancarboxylicacid (2R)-5-Oxotetrahydrofuran-2-carboxylicacid 2-furancarboxylicacid,tetrahydro-5-oxo-,(2R)- 5-Oxo-tetrahydro-furan-2-carboxylic (R)-(-)-5-oxotetrahydrofuran-2-carboxylicacid -butyrolactone -carboxylicacid -furancarboxylicacid (theta)-2-furancarboxylicaci (r)-(-)-5-oxo-2-tetrahydrofuroicacid (r)-gamma-carboxy-gamma-butyrolactone 5-oxo-2-tetrahydrofurancarboxylicacid (r)-(-)-gamma-carboxy-gamma-butyrolactone (r)-5-oxotetrahydrofuran-2-carboxylicacid d-5-oxo-2-tetrahydrofurancarboxylicacid(r-) (r)-(-)-5-oxo-2-tetrahydrofurancarboxylicacid (r)-(-)-tetrahydro-5-oxo-2-furanecarboxylicacid -butyrolactone,(r)-5-oxotetrahydro-2-furancarboxylicacid

Molecular Formula: C5H6O4

Molecular Weight: 130.1

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > APIs and Their Salts > Nervous System Drugs

Product Description:

(R)-5-Oxotetrahydrofuran-2-carboxylic acid is a chiral γ-lactone derivative featuring a carboxylic acid functional group. It serves as a crucial chiral building block in organic synthesis, particularly for the preparation of pharmaceuticals. Its primary and most significant application is as a key intermediate in the synthesis of Levetiracetam, a widely used antiepileptic drug (AED) belonging to the racetam class. The (R)-enantiomer of this lactone is essential for constructing the core pyrrolidinone structure of Levetiracetam with the correct stereochemistry, which is vital for its pharmacological activity. The synthesis typically involves further steps including amidation and introduction of an alkyl side chain. This compound exemplifies the importance of chiral intermediates in modern asymmetric drug synthesis. Its use is specific to the production pathway of a major central nervous system (CNS) active pharmaceutical ingredient (API), rather than being a general-purpose synthetic reagent.

Physical Properties

Melting Point: 71-73 °C(lit.)

Boiling Point: 165-167 °C/0.3 mmHg(lit.)

Flash Point: 184.6 °C

Density: 1.469 g/cm3