(2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone
[CAS# 115250-38-9]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Ketones
• Name: (2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone
• Molecular Formula: C₃₅H₃₆O₆
• Molecular Weight: 552.66
• CAS Registry Number: 115250-38-9
• SMILES: C1C(=O)[C@@H]([C@H]([C@@H]([C@]1(COCC2=CC=CC=C2)O)OCC3=CC=CC=C3)OCC4=CC=CC=C4)OCC5=CC=CC=C5

Properties

• Density: 1.23±0.1 g/cm³, Calc.^*
• Melting point: 84-85 °C
• Index of Refraction: 1.624, Calc.^*
• Boiling Point: 681.9±55.0 °C (760 mmHg), Calc.^*
• Flash Point: 214.1±25.0 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

(2R,3S,4S,5S)-5-Hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone is a complex organic compound known for its unique molecular structure and potential applications in the fields of medicinal chemistry and material science. This molecule consists of a cyclohexanone ring, which is substituted with multiple phenylmethoxy groups, a hydroxyl group, and a methyl group. The presence of these functional groups imparts distinct electronic and steric properties to the compound, influencing its reactivity and interactions with biological targets.

The discovery of this chemical substance is part of ongoing research aimed at developing molecules with specific biological activities. The hydroxy and phenylmethoxy groups enhance the compound's ability to interact with various proteins and enzymes, making it a potential candidate for therapeutic applications. The stereochemistry of the molecule, with its specific configuration at the 2R, 3S, 4S, and 5S positions, suggests that its three-dimensional shape could be crucial for its biological activity. Such stereochemical precision is often important for ensuring selectivity and potency in drug design.

One of the primary applications of (2R,3S,4S,5S)-5-hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone lies in its potential as an intermediate in the synthesis of bioactive compounds. The presence of phenylmethoxy groups increases the molecule's lipophilicity, which can enhance its ability to penetrate biological membranes. This characteristic is desirable for the development of drugs that need to interact with intracellular targets, such as enzymes or receptors. Furthermore, the hydroxyl group and methyl group may provide additional points of interaction, potentially improving the compound's bioactivity and selectivity.

Research has indicated that cyclohexanone derivatives, particularly those with functional groups like phenylmethoxy, can exhibit a wide range of biological activities, including antibacterial, anti-inflammatory, and anticancer effects. The presence of multiple aromatic groups in this compound enhances its ability to bind to target molecules, potentially making it an effective agent in inhibiting the activity of specific enzymes or signaling pathways involved in disease processes. Studies on similar structures have shown that such molecules can act as enzyme inhibitors or receptor antagonists, making them candidates for treating conditions such as cancer, inflammation, and infectious diseases.

Additionally, the compound's structural complexity and the functionality of its phenylmethoxy substituents make it a promising candidate for material science applications. Its ability to form stable molecular structures and interactions suggests that it could be useful in the design of new polymers, coatings, or other materials where high stability and controlled reactivity are required. The phenylmethoxy groups, in particular, are known to confer rigidity and stability, making the compound suitable for use in creating advanced materials that need to maintain their properties under varying environmental conditions.

The ongoing exploration of (2R,3S,4S,5S)-5-hydroxy-2,3,4-tris(phenylmethoxy)-5-[(phenylmethoxy)methyl]-cyclohexanone continues to highlight its versatility. Researchers are working to optimize its synthesis and explore its full potential in both pharmaceutical and material science applications, with the goal of developing new treatments and high-performance materials that can meet the needs of modern science.

References

2017. Facile Synthesis of N-Substituted 4-Amino-6-methyl Resorcinols from Polysubstituted Cyclohexanone. Synlett.
DOI: 10.1055/s-0036-1590817

2005. Reduction of α,α-Dihalo Ketones. Science of Synthesis.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-026-00090