The Chemical Profile of Boc-D-2,3,4,5,6-Pentafluorophenylalanine: A Key Intermediate
In the realm of advanced organic synthesis, particularly for pharmaceutical and biochemical applications, certain molecules stand out due to their unique structural features and versatility. Boc-D-2,3,4,5,6-pentafluorophenylalanine (CAS 136207-26-6) is one such critical intermediate. This compound represents a fusion of an amino acid backbone with significant fluorination, all while being presented in a protected and chiral form suitable for sophisticated chemical processes.
Let's delve into its chemical profile: The molecule is an derivative of phenylalanine, a naturally occurring aromatic amino acid. However, the key distinction lies in the pentafluorophenyl moiety attached to the beta-carbon. This group, consisting of a benzene ring where all five hydrogen atoms are replaced by fluorine atoms, imparts distinct electronic and steric properties. Fluorine, being the most electronegative element, strongly influences the electron density of the aromatic ring and adjacent atoms. This can lead to altered reactivity, increased lipophilicity, and enhanced metabolic stability in molecules incorporating this structure.
The 'Boc' (tert-butyloxycarbonyl) group serves as a protecting group for the alpha-amino function. In peptide synthesis and other amine-involved reactions, protecting groups are essential to prevent unwanted side reactions and to control the sequence of chemical transformations. The Boc group is widely used due to its ease of introduction and removal under specific acidic conditions, making it compatible with many synthetic strategies.
The 'D-' designation signifies the stereochemistry at the alpha-carbon. While natural amino acids are predominantly in the L-configuration, D-amino acids are increasingly incorporated into therapeutic peptides to confer resistance to enzymatic degradation by proteases, thereby extending their in vivo half-life. The availability of Boc-D-2,3,4,5,6-pentafluorophenylalanine in this specific chiral form is thus critical for targeted applications.
As a high-purity chemical intermediate (typically ≥97%), this compound is sought after by researchers and manufacturers for its role in:
- Peptidomimetics: Designing molecules that mimic the structure and function of natural peptides but with improved pharmacological properties.
- API Synthesis: Serving as a chiral building block in the multi-step synthesis of complex active pharmaceutical ingredients.
- Medicinal Chemistry: Introducing fluorine and specific amino acid structures to modify drug candidate properties for better efficacy and pharmacokinetics.
For organizations looking to buy Boc-D-2,3,4,5,6-pentafluorophenylalanine, partnering with a reliable manufacturer and supplier, especially one based in China, can offer significant advantages in terms of cost and consistent supply. We are committed to providing this high-quality intermediate, backed by stringent quality control measures, to support your critical synthetic projects. Our focus on delivering premium chemical reagents ensures that your research and development efforts are supported by the finest materials available on the market.
Perspectives & Insights
Core Pioneer 24
“However, the key distinction lies in the pentafluorophenyl moiety attached to the beta-carbon.”
Silicon Explorer X
“This group, consisting of a benzene ring where all five hydrogen atoms are replaced by fluorine atoms, imparts distinct electronic and steric properties.”
Quantum Catalyst AI
“Fluorine, being the most electronegative element, strongly influences the electron density of the aromatic ring and adjacent atoms.”