Benzyl (Z)-7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoate
[CAS 136790-77-7]

Identification

• Classification: Organic raw materials >> Carboxylic compounds and derivatives >> Carboxylic esters and their derivatives
• Name: Benzyl (Z)-7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoate
• Synonyms: (Z)-Benzyl 7-((1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-((tetrahydro-2H-pyran-2-yl)oxy)cyclopentyl)hept-5-enoate
• Molecular Formula: C₃₂H₄₈F₂O₆
• Molecular Weight: 566.72
• CAS Registry Number: 136790-77-7
• SMILES: CCCCC(C(CC[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=CCCCC(=O)OCC2=CC=CC=C2)O)OC3CCCCO3)O)(F)F

Properties

• Solubility: Insoluble (6.8E^-4 g/L) (25 °C), Calc.^*
• Density: 1.15±0.1 g/cm³ (20 °C 760 Torr), Calc.^*
• Boiling point: 662.1±55.0 °C 760 mmHg (Calc.)^*
• Flash point: 354.2±31.5 °C (Calc.)^*
• Index of refraction: 1.528 (Calc.)^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H350
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

Benzyl (Z)-7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoate is a highly functionalized synthetic organic compound featuring a long-chain ester linked to a substituted cyclopentane core bearing multiple oxygenated and fluorinated substituents. The molecule incorporates several key structural elements, including a benzyl ester group, a cis-configured (Z) carbon–carbon double bond within a heptenoate chain, a polyfunctional cyclopentane ring system, and a difluoro-substituted aliphatic side chain.

The structure reflects a design motif commonly encountered in advanced synthetic lipid analogues and prostanoid-related chemistry, where a central cyclopentane ring is substituted with multiple stereochemically defined side chains. The presence of four stereocenters in the cyclopentyl core indicates a highly controlled stereochemical architecture, which is typically achieved through stereoselective synthetic routes or derivatization from chiral intermediates. Stereochemistry plays a crucial role in such systems, as spatial arrangement strongly influences conformational behavior and intermolecular interactions.

The benzyl ester functionality is formed by esterification of a carboxylic acid with benzyl alcohol. Benzyl esters are widely used in organic synthesis as protecting groups for carboxylic acids due to their stability under neutral and basic conditions and their ability to be removed under hydrogenolysis conditions. In complex molecule synthesis, benzyl esters often serve as temporary modifications to modulate reactivity or facilitate purification.

The hept-5-enoate chain contains a double bond in the Z configuration, indicating a cis relationship between substituents across the alkene. Geometric isomerism in unsaturated chains is important because it influences molecular shape, introducing a bend in the carbon backbone. This structural feature is commonly found in lipid-like molecules and contributes to their conformational diversity and biological recognition properties.

The cyclopentane core is heavily substituted, bearing hydroxyl groups and an ether linkage to a tetrahydropyran (THP) protecting group. The THP group is a well-established protecting group for alcohols in organic synthesis, used to temporarily mask hydroxyl functionality during multi-step synthetic sequences. Its presence indicates that the molecule is likely an intermediate in a synthetic pathway where selective protection and deprotection steps are required to control reactivity.

The difluoro-substituted octyl side chain introduces significant electronic and physicochemical modification. Fluorine atoms strongly influence molecular properties due to their high electronegativity and small size. The presence of geminal difluoro substitution at one carbon can increase metabolic stability, alter lipophilicity, and modify conformational preferences of the aliphatic chain. Fluorinated substituents are widely used in medicinal chemistry and advanced organic synthesis to tune molecular behavior.

The multiple hydroxyl groups present in the structure contribute polarity and hydrogen-bonding capability. These functional groups can participate in intermolecular interactions that influence solubility, aggregation, and potential biological recognition. In combination with the hydrophobic hydrocarbon framework and ester linkage, the molecule exhibits amphiphilic character typical of lipid-derived synthetic analogues.

From a synthetic perspective, molecules of this complexity are generally constructed through multi-step sequences involving stereoselective carbon–carbon bond formation, protecting group strategies, and functional group interconversion. The use of protecting groups such as tetrahydropyranyl ethers and benzyl esters allows selective manipulation of reactive hydroxyl and carboxyl functionalities during assembly of the final structure.

Compounds with structural similarity to this molecule are often encountered in the field of lipid chemistry and prostaglandin analogue synthesis, where cyclopentane-based scaffolds serve as core frameworks for biologically active molecules. While the specific biological activity of this compound is not inherent from structure alone, such architectures are frequently explored in medicinal chemistry due to their resemblance to endogenous lipid mediators.

Overall, benzyl (Z)-7-[(1R,2R,3R,5S)-2-(4,4-difluoro-3-hydroxyoctyl)-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yl)oxy]cyclopentyl]hept-5-enoate is a complex, stereochemically rich, multifunctional ester incorporating fluorinated, protected, and hydroxylated motifs. Its structure reflects modern strategies in complex molecule synthesis, particularly those used in the controlled assembly of lipid-like frameworks with defined stereochemistry and functional group protection.