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Boc-D-3-Bromophenylalanine丨CAS 261360-77-4 Supplier in China
Boc-D-3-Bromophenylalanine is an N-protected derivative of D-3-bromophenylalanine, combining a tert-butoxycarbonyl (Boc) protecting group with a bromine substituent at the 3-position of the aromatic ring. Its D-configuration provides defined stereochemistry, while the Boc group helps protect the amino functionality during multistep synthesis. The aromatic bromine also offers a potential site for further chemical modification, making this compound useful in specialized amino acid chemistry, peptide research, and organic synthesis.
Chemical Identifiers
| InChI | InChI=1S/C14H18BrNO4/c1-14(2,3)20-13(19)16-11(12(17)18)8-9-5-4-6-10(15)7-9/h4-7,11H,8H2,1-3H3,(H,16,19)(H,17,18)/t11-/m1/s1 |
| InChI Key | FBUDYESOPLBQIR-LLVKDONJSA-N |
| Smiles | CC(C)(C)OC(=O)N[C@H](CC1=CC(=CC=C1)Br)C(=O)O |
| EC No. | 807-895-4 |
| MDL No. | MFCD01317704 |
| PubChem CID | 7006629 |
Applications
Applications in Peptide Synthesis
Boc-D-3-Bromophenylalanine can serve as a protected amino acid building block in peptide synthesis and related research. The Boc group helps control the reactivity of the amino group during selected synthetic steps, while the D-configuration allows researchers to introduce a non-natural stereochemical feature into peptide sequences. Its suitability depends on the coupling strategy, deprotection conditions, and requirements of the target peptide.
Applications in Medicinal Chemistry
In medicinal chemistry, Boc-D-3-Bromophenylalanine can be used as an intermediate for preparing structurally diverse amino-acid-derived compounds. The combination of D-stereochemistry and aromatic bromination provides opportunities to investigate molecular structure and develop analogues for research. The Boc protecting group also supports stepwise synthesis when temporary amino protection is required.
Applications in Cross-Coupling Reactions
Applications in Chiral Building Block Development
Boc-D-3-Bromophenylalanine is relevant to synthesis projects requiring a protected D-amino acid with an additional functional handle. Its defined stereochemistry supports the preparation of stereochemically specified intermediates, while the Boc group can be removed when the free amino functionality is needed for subsequent reactions. This combination is useful in multistep route development and specialty compound synthesis.
