Boc-D-phenylalaninol is a protected amino alcohol derivative of the phenylalanine family, featuring a benzyl side chain attached to a chiral carbon bearing a primary alcohol and an amino functionality converted to a Boc carbamate. The molecule contains a tert-butoxycarbonyl (Boc) protecting group on the nitrogen, which masks the free amino group and supports chemoselective handling of the alcohol during peptide-related or coupling chemistry. In synthetic workflows, this protected D-phenylalaninol is used as a precursor for preparing amino alcohol-containing building blocks and for constructing more complex peptide or peptidomimetic structures where the free hydroxyl provides a functional handle for further derivatization.
CAT No: CP26168
CAS No:106454-69-7
Synonyms/Alias:N-Boc-D-phenylalaninol;106454-69-7;Boc-D-phenylalaninol;(R)-tert-Butyl(1-hydroxy-3-phenylpropan-2-yl)carbamate;N-(tert-Butoxycarbonyl)-D-phenylalaninol;(R)-2-(Boc-amino)-3-phenyl-1-propanol;MFCD00216472;ST50307737;(R)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol;(R)-(+)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol;tert-butylN-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate;PubChem5739;AC1Q1MSR;N-t-BOC-D-Phenylalaninol;KSC180I8H;SCHEMBL257912;CTK0I0483;LDKDMDVMMCXTMO-GFCCVEGCSA-N;MolPort-001-793-349;ACN-S003441;ACT04153;ZINC2558962;ANW-15350;FC1221;ZINC02558962
Boc-D-phenylalaninol is a D-configured phenylalanine-derived amino alcohol protected as a Boc carbamate, providing a stable, bench-friendly building block for stereodefined nitrogen-carbon frameworks. The combination of a protected amine and a free primary alcohol makes this reagent particularly useful for assembling chiral intermediates where controlled stereochemistry and orthogonal functionality are required. In synthetic and medicinal chemistry workflows, it serves as a convenient precursor to amino-alcohol motifs used in peptidomimetic design and downstream derivatization.
1. Chiral Amino Alcohol Intermediates
Boc-D-phenylalaninol is widely used by medicinal chemistry and process development teams to access stereodefined amino alcohol scaffolds that can be elaborated into more complex chiral intermediates. The Boc-protected nitrogen allows selective transformations at the alcohol functionality, supporting stepwise construction of nitrogen-containing motifs while maintaining D-stereochemical integrity. This makes the compound a practical choice for preparing libraries of analogs and for producing well-defined intermediates used in structure-activity relationship (SAR) synthesis.
2. Peptidomimetic And Scaffold Building
Boc-D-phenylalaninol supports the preparation of peptidomimetic and constrained scaffold fragments where an amino alcohol can mimic key geometric and hydrogen-bonding features of peptide-like backbones. Research groups developing non-peptide or backbone-modified ligands often require chiral building blocks that can be functionalized without disturbing the protected amine, and the Boc group provides a reliable handle during multi-step assembly. The resulting derivatives are commonly used as precursors for further coupling, cyclization, or installation of substituents that tune physicochemical properties.
3. Pharmaceutical Intermediate Derivatization
Boc-D-phenylalaninol is frequently selected as a pharmaceutical intermediate for routes that convert the free alcohol into activated derivatives, enabling subsequent coupling to electrophiles or incorporation into larger synthetic sequences. The protected carbamate form helps manage reactivity during intermediate synthesis, while the primary alcohol provides a direct point of functional diversification. Industrial and custom synthesis laboratories use this reagent to streamline access to chiral, nitrogen-containing intermediates that can be carried forward into candidate-manufacturing chemistry.
4. Stereocontrolled Organic Synthesis
Boc-D-phenylalaninol is also used in general stereocontrolled organic synthesis when a D-configured phenylalanine-derived amino alcohol is required as a starting material for asymmetric or stereospecific transformations. Chemists value the combination of a Boc-protected amine and an unprotected alcohol because it enables selective chemistry planning across steps, reducing the need for additional protection/deprotection cycles. This supports efficient preparation of chiral intermediates used in research-grade synthesis, including route scouting and intermediate optimization for complex target molecules.
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