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Bulk Order Boc-4-Bromo-D-beta-phenylalanine丨CAS 261165-06-4
Boc-4-Bromo-D-beta-phenylalanine is a protected D-beta-amino acid derivative featuring a tert-butoxycarbonyl (Boc) protecting group and a bromine substituent at the 4-position of the aromatic ring. Its beta-amino acid backbone differs from that of conventional alpha-amino acids, offering additional structural diversity for molecular design and synthesis. The combination of defined stereochemistry, amino protection, and aromatic bromination makes this compound a potential building block for beta-peptide research, medicinal chemistry, and specialized organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(8-12(17)18)9-4-6-10(15)7-5-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m0/s1 |
| InChI Key | ZAMLGGRVTAXBHI-NSHDSACASA-N |
| Smiles | CC(C)(C)OC(=O)N[C@@H](CC(=O)O)C1=CC=C(C=C1)Br |
| EC No. | |
| MDL No. | MFCD03419292 |
| PubChem CID | 2734491 |
Applications
Applications in Peptide Synthesis
Boc-4-Bromo-D-beta-phenylalanine can be considered for the preparation of beta-peptides and other compounds containing beta-amino acid residues. The Boc group temporarily protects the amino functionality during selected synthetic steps, while the D-configuration provides a defined stereochemical feature for molecular design. Its use depends on the target sequence, coupling chemistry, and compatibility with the chosen protection and deprotection strategy.
Applications in Medicinal Chemistry
In medicinal chemistry research, this compound can serve as an intermediate for preparing structurally diverse amino-acid-derived molecules. The beta-amino acid backbone provides an alternative arrangement of functional groups compared with conventional alpha-amino acids, while the brominated aromatic ring offers opportunities for further chemical modification. These features may support the exploration of molecular analogues and structure–activity relationships.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
Boc-4-Bromo-D-beta-phenylalanine is relevant to synthesis projects requiring a protected beta-amino acid with defined D-configuration. The Boc group allows controlled access to the amino functionality for subsequent coupling or derivatization, while the aromatic bromine provides a potential handle for further functionalization. This combination can support the development of specialized intermediates for peptide and pharmaceutical research.
