(-)-Corey aldehyde benzoate
[CAS# 39746-01-5]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (-)-Corey aldehyde benzoate
• Synonyms: [3aR(3aa,4a,5b,6aa)]-(-)-5-(Benzoyloxy)hexahydro-2-oxo-2H-cyclopenta[b]furan-4-carboxaldehyde
• Molecular Formula: C₁₅H₁₄O₅
• Molecular Weight: 274.27
• CAS Registry Number: 39746-01-5
• SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OC(=O)C3=CC=CC=C3)C=O

Properties

• Melting point: 128-138 °C
• alpha: -85 ° (c=1, MeOH)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P280

Discovery and Applications

(-)-Corey aldehyde benzoate is an important compound in the field of organic chemistry, known for its unique structural characteristics and diverse applications in synthetic pathways. The discovery of (-)-Corey aldehyde benzoate is rooted in the study of chiral aldehydes and their derivatives, which have gained prominence due to their usefulness in the synthesis of biologically active molecules.

The compound was synthesized as part of the exploration of methods to obtain chiral intermediates for pharmaceuticals and other fine chemicals. The development of efficient synthetic routes has been a critical area of research, leading to the formation of (-)-Corey aldehyde benzoate through a series of stereoselective reactions. These reactions typically involve the use of chiral catalysts or reagents that facilitate the formation of the desired stereochemistry, ensuring high enantiomeric purity of the final product.

One of the significant applications of (-)-Corey aldehyde benzoate lies in its role as an intermediate in the synthesis of various biologically active compounds. The compound's structure, which features a benzoate group, makes it an attractive building block for the development of pharmaceuticals that target specific biological pathways. Researchers have utilized (-)-Corey aldehyde benzoate to create derivatives that exhibit pharmacological activities, including anti-inflammatory and anti-cancer properties.

In addition to its applications in medicinal chemistry, (-)-Corey aldehyde benzoate has potential uses in the development of agrochemicals. Its ability to undergo further transformations allows chemists to modify the molecule to enhance its biological activity against pests or pathogens. This versatility makes it a valuable compound in the ongoing search for effective agricultural solutions.

Furthermore, (-)-Corey aldehyde benzoate serves as a model compound in the study of reaction mechanisms and stereochemistry. Its well-defined structure provides an opportunity for chemists to explore the intricacies of chemical reactivity and selectivity, contributing to the broader understanding of organic reactions.

In summary, (-)-Corey aldehyde benzoate is a notable compound in organic chemistry, distinguished by its chiral nature and functional versatility. Its applications extend beyond medicinal chemistry into the realm of agrochemicals, making it a significant compound for research and development. As studies continue to unveil its potential, (-)-Corey aldehyde benzoate remains an important building block in the synthesis of complex organic molecules.

References

2010. Synthesis of ONO-4819. Synfacts.
DOI: 10.1055/s-0029-1219301

2010. Tafluprost. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0221