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Specifications
| Appearance: | white or off white powder |
| Assay (calculated by free alkali): | 66-72% |
| Specific optical rotation: | +9 to +14 deg |
| Identification: | The retention time of the major peak of the sample solution corresponds to that of the system suitability solution, as obtained in the diastereoisomer (remove the blank solvent peak). IR spectrum sample should concordant with the spectrum of standard |
| Water: | 1.0% max |
| Trifluoroacetic acid: | 28-32% |
| Diastereoisomer: | 0.2% max |
| Enantiomer: | 0.2% max |
| Isoblutyl bromide: | 0.1% max |
| 3-methyl butylamine: | 1.0% max |
| Dichloromethane: | 0.06% max |
| Methyl tert-butyl ether: | 0.5% max |
| Hexane: | 0.029% max |
| Isopropyl ether: | 1.0% max |
| Tetrahydrofuran: | 0.072% max |
| N-heptane: | 0.5% max |
| Methyl cyclohexane: | 0.118% max |
| Ethyl benzene: | 0.5% max |
Applications
1. Asymmetric Synthesis
Used as a chiral building block or reagent in enantioselective synthesis to introduce chiral centers.
Facilitates enantioselective carbon–carbon bond formations, such as in allylation, alkylation, and boration reactions.
The chiral boronate ester moiety provides high stereocontrol, crucial for synthesizing enantiomerically pure compounds in pharmaceuticals and fine chemicals.
2. Chiral Auxiliary or Ligand Precursor
Serves as a chiral auxiliary or ligand precursor in catalytic asymmetric reactions.
Can coordinate with metals or participate in catalytic cycles to induce chirality in target molecules.
3. Synthesis of Chiral Amino Acid Derivatives
Utilized in the preparation of chiral amino acid analogs, such as boron-containing leucine derivatives, which are valuable in medicinal chemistry.
These boron-modified amino acids can serve as enzyme inhibitors, molecular probes, or building blocks for peptides with enhanced biological activity.
4. Pharmaceutical and Medicinal Chemistry
Key intermediate in the synthesis of boron-containing drugs, including protease inhibitors and anticancer agents.
The controlled chirality is vital for drug efficacy and reduced side effects.
Benefits
1. High Enantioselectivity
The compound enables the efficient transfer of chirality in synthesis, providing high enantiomeric excess in products.
Pinanediol protection stabilizes the boron center, enhancing selectivity.
2. Improved Stability and Handling
The pinanediol boronate ester form is more chemically stable and easier to handle than free boronic acids or boranes.
The trifluoroacetate salt form improves solubility and reaction control.
3. Versatility in Synthesis
Applicable in a wide range of asymmetric transformations.
Allows access to complex chiral molecules with precise stereochemical control.
4. Facilitates Drug Development
Supports the synthesis of chirally pure intermediates for pharmaceuticals.
Enhances the potential for boron-based drug candidates with improved biological activity.
Conclusion
(R)-BoroLeu-(+)-Pinanediol trifluoroacetate (CAS 179324-87-9) is a chiral boron reagent designed for use in enantioselective organic synthesis. Its unique structure, combining the (R)-leucine framework with a pinanediol boronate ester and trifluoroacetate salt, provides excellent stereochemical control, stability, and synthetic versatility. This makes it highly valuable in the production of chiral amino acid derivatives, boron-containing pharmaceuticals, and as a chiral auxiliary or ligand precursor in catalytic asymmetric reactions.
