(+)-Corey lactone 5-(4-phenylbenzoate)
[CAS# 39265-57-1]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ester intermediate
• Name: (+)-Corey lactone 5-(4-phenylbenzoate)
• Synonyms: (+)-Corey lactone 4-phenylbenzoate alcohol; (3aS,4R,5S,6aR)-Hexahydro-4-hydroxymethyl-5-(4-phenylbenzyloxy)cyclopenta[b]furan-2-one
• Molecular Formula: C₂₁H₂₀O₅
• Molecular Weight: 352.38
• CAS Registry Number: 39265-57-1
• SMILES: C1[C@@H]2[C@@H](CC(=O)O2)[C@@H]([C@H]1OC(=O)C3=CC=C(C=C3)C4=CC=CC=C4)CO

Properties

• Density: 1.32
• Melting point: 134-136 °C

Discovery and Applications

(+)-Corey lactone 5-(4-phenylbenzoate) is a synthetic derivative of Corey lactone, a compound introduced by the renowned chemist E.J. Corey. The discovery of Corey lactone was a significant milestone in the development of stereoselective organic synthesis. Corey’s work in this area earned him the Nobel Prize in Chemistry in 1990. The addition of a 4-phenylbenzoate group to (+)-Corey lactone enhances its utility in chemical synthesis by modifying its reactivity and providing further opportunities for functionalization.

(+)-Corey lactone 5-(4-phenylbenzoate) is synthesized by esterifying Corey lactone with 4-phenylbenzoic acid, often using activating agents like dicyclohexylcarbodiimide (DCC) to facilitate the reaction. This esterification preserves the stereochemistry of the original Corey lactone, while the 4-phenylbenzoate group introduces aromatic functionality. The result is a compound with increased versatility in organic synthesis, where it can be used as a building block or intermediate in constructing more complex molecules.

One of the primary applications of (+)-Corey lactone 5-(4-phenylbenzoate) is in the field of asymmetric synthesis. Its chiral nature makes it valuable for creating enantioselective reactions, where the control of stereochemistry is critical. The compound is particularly useful in the synthesis of bioactive molecules, such as natural products and pharmaceuticals. The phenylbenzoate group can also impart unique properties to the final products, influencing their reactivity and biological activity.

In addition to its role in asymmetric synthesis, (+)-Corey lactone 5-(4-phenylbenzoate) has been explored in catalysis. Its chiral backbone allows it to serve as a ligand or catalyst in reactions that require high stereocontrol. This capability makes it a key reagent in developing methods for producing chiral compounds, which are essential in many areas of drug development and material science.

Overall, (+)-Corey lactone 5-(4-phenylbenzoate) represents an important tool in modern synthetic chemistry, with broad applications in creating complex, stereochemically pure molecules. Its discovery and continued use highlight the impact of stereocontrolled synthesis in advancing organic chemistry.

References

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