Boc-2-Trifluoromethyl-D-Phenylalanine is a protected, non-natural amino acid derivative featuring a phenylalanine backbone bearing a 2-(trifluoromethyl) substituent on the alpha carbon and a D stereochemical configuration as indicated by the product name. The molecule contains a Boc-protected amino group and a free carboxyl functional group, with the trifluoromethylated aromatic side chain providing strong electron-withdrawing character and increased lipophilicity relative to unsubstituted phenylalanine. It is used as a building block for stepwise peptide synthesis and structure-activity or labeling studies where incorporation of a fluorinated, stereodefined amino acid residue is required to tune physicochemical properties and enable downstream derivatization.
CAT No: CP16605
CAS No:346694-78-8
Synonyms/Alias:346694-78-8;Boc-D-2-Trifluoromethylphenylalanine;Boc-D-Phe(2-CF3)-OH;N-Boc-2-trifluoromethyl-D-phenylalanine;boc-d-2-trifluoromethylphe;boc-2-trifluoromethyl-d-phenylalanine;(R)-2-((tert-butoxycarbonyl)amino)-3-(2-(trifluoromethyl)phenyl)propanoicacid;Boc-2-(trifluoromethyl)-D-phenylalanine;n-boc-2-(trifluoromethyl)-d-phenylalanine;boc-d-2-trifluoromethyl-phe-oh;(2r)-2-[(tert-butoxycarbonyl)amino]-3-[2-(trifluoromethyl)phenyl]propanoicacid;2-(trifluoromethyl)-d-phenylalanine,n-bocprotected;(r)-2-(tert-butoxycarbonylamino)-3-(2-(trifluoromethyl)phenyl)propanoicacid;(r)-2-tert-butoxycarbonylamino-3-(2-trifluoromethyl-phenyl)-propionicacid;Boc-L-phe(2-CF3)-OH;15009_ALDRICH;SCHEMBL3557995;15009_FLUKA;CTK8C5225;MolPort-001-777-526;XKMOOODKNPYTEE-LLVKDONJSA-N;ZINC2386874;ANW-74824;PC8354;AB10282
Boc-2-Trifluoromethyl-D-Phenylalanine is a D-configured, non-proteinogenic amino acid building block bearing a Boc-protecting group on the amino functionality and a sterically and electronically distinctive 2-trifluoromethyl substituent on the side chain. This fluorinated, conformationally biasing motif is frequently leveraged in medicinal chemistry and peptide/peptidomimetic synthesis to probe structure-activity relationships and to tune physicochemical properties. As a protected amino acid, it is commonly handled as a defined intermediate for downstream coupling into larger frameworks under peptide synthesis conditions.
1. Peptidomimetic Building Blocks
Boc-2-Trifluoromethyl-D-Phenylalanine is used by medicinal chemistry and process research groups to assemble peptidomimetic scaffolds where incorporation of a fluorinated, bulky side chain is desired for SAR studies. The D-stereochemistry supports the preparation of stereochemically defined analogs used to evaluate how backbone stereochemical variation influences conformation and functional readouts in chemical biology campaigns. The Boc protection provides a convenient, stable amino handle for sequential construction of multi-unit intermediates prior to final deprotection and purification steps.
2. Stereodefined Peptide Synthesis
Boc-2-Trifluoromethyl-D-Phenylalanine serves as a protected amino acid input for custom peptide synthesis workflows that require a non-natural residue with a controlled stereochemical configuration. Research teams building short peptides, constrained analogs, or backbone-modified sequences rely on this reagent to introduce the 2-trifluoromethyl group at a specific position, enabling systematic variation of side-chain electronics and sterics across a peptide series. The Boc-protected format supports stepwise assembly strategies in which the residue is introduced as a discrete, well-defined coupling partner.
3. Pharmaceutical Intermediate Development
Boc-2-Trifluoromethyl-D-Phenylalanine is also used as a pharmaceutical intermediate building block during the synthesis of fluorinated small molecules and amino-acid-derived fragments for lead optimization. Process chemists and synthetic development teams favor this reagent when a D-configuration and a trifluoromethyl-substituted phenylalanine motif must be carried through multiple synthetic steps with minimal ambiguity in stereochemical outcome. The protected amino functionality helps streamline downstream transformations by maintaining a controlled functional-group profile during intermediate elaboration.
4. Structure-Activity Relationship Probing
Boc-2-Trifluoromethyl-D-Phenylalanine is commonly selected for SAR and analog libraries where fluorinated substitutions are introduced to map the contribution of side-chain bulk and electron-withdrawing effects. Chemical biology and medicinal chemistry groups use it to generate matched series of compounds that differ primarily at the fluorinated residue position, supporting structure-property investigations tied to binding-site geometry and conformational preferences. Its defined D-stereochemistry and protected amino group make it practical for parallel synthesis and comparative characterization workflows.
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