Boc-L-Tyr(Boc)-OH is a protected amino acid derivative based on L-tyrosine in which the α-amino group is carbamated as a Boc (tert-butoxycarbonyl) group and the phenolic side chain is additionally protected as a second Boc-protected functionality. The molecule therefore bears a free carboxylic acid (-COOH) along with Boc-protected amino and Boc-protected phenolic oxygen, and its stereochemistry at the α-carbon is specified as L by the product name. In peptide synthesis workflows, this orthogonally protected tyrosine analogue is used as a stepwise building block to control chemoselectivity during coupling and to support the incorporation of a protected tyrosine side chain for subsequent deprotection and downstream peptide or conjugate assembly.
CAT No: CP25597
CAS No:20866-48-2
Synonyms/Alias:BOC-TYR(BOC)-OH;20866-48-2;AmbotzBAA1444;Boc-L-Tyr(Boc)-OH;N,O-BisBoc-(S)-tyrosine;N,O-Bis-Boc-(S)-tyrosine;SCHEMBL1087185;CTK8F8295;MolPort-003-983-080;MRYIHKCPPKHOPJ-AWEZNQCLSA-N;ZINC2391152;0673AB;AKOS015924175;AKOS016002099;MCULE-9218719859;RL02583;N,O-Bis(tert-butoxycarbonyl)-L-tyrosine;AJ-35731;AK-49558;KB-93631;Boc-Tyr(Boc)-OH;N,O-di-Boc-L-tyrosine;FT-0638053;K-6035;Q-101633
Chemical Name:N-alpha,O-Bis-t-Butyloxycarbonyl-L-tyrosine
Boc-L-Tyr(Boc)-OH is a protected tyrosine amino acid derivative bearing an N-terminal Boc protecting group and a Boc-protected phenolic side chain, providing orthogonality and reduced side-chain reactivity during peptide assembly. The L-configuration at the amino acid stereocenter supports its use as a stereochemically defined building block for controlled incorporation into peptide sequences. This double-protected format is commonly selected when minimizing phenol oxidation and suppressing undesired side reactions are important for downstream coupling and purification workflows.
1. Solid-Phase Peptide Synthesis
Boc-L-Tyr(Boc)-OH is used by peptide synthesis groups to introduce a tyrosine residue with both the amino group and the phenolic side chain protected, helping maintain chemoselectivity during stepwise assembly. In solid-phase peptide synthesis workflows, the Boc-protected amino functionality supports segment coupling strategies where side-chain protection is essential to prevent phenolic participation in coupling, base-promoted side reactions, or oxidative processes. Peptide manufacturers and academic peptide labs frequently rely on this protected tyrosine building block when preparing Tyr-containing sequences that require robust handling through repeated deprotection/coupling cycles and when minimizing side-chain heterogeneity is critical for consistent product quality.
2. Modified Peptide Building Block
Boc-L-Tyr(Boc)-OH is also applied in the preparation of modified peptides and peptide intermediates where the tyrosine phenol must remain masked until late-stage functionalization. Researchers developing tyrosine-dependent constructs often choose this protected derivative to keep the phenolic oxygen inert during earlier synthetic steps, then reveal the phenol under appropriate deprotection conditions for subsequent derivatization such as phosphorylation-mimetic chemistry, conjugation-ready phenol activation, or installation of tyrosine-based motifs. This makes the reagent a practical choice for peptide library synthesis and custom peptide manufacturing projects that require controlled timing of phenol exposure to improve reproducibility across multiple analogs.
3. Pharmaceutical Intermediate Development
Boc-L-Tyr(Boc)-OH is used in medicinal chemistry and pharmaceutical intermediate development to generate tyrosine-containing intermediates with protected functionality that can be carried through multi-step synthesis toward peptide-like or peptidomimetic scaffolds. Process development teams value the double-protection pattern because it reduces the likelihood of phenol-related side reactions during intermediate transformations and purification. The resulting protected tyrosine unit can be incorporated into larger synthetic sequences where downstream coupling, fragment assembly, or later-stage derivatization requires a stable, well-defined building block that tolerates common organic synthesis conditions used in intermediate manufacturing workflows.
4. Peptide Purification Consistency
Boc-L-Tyr(Boc)-OH supports improved consistency in Tyr-containing peptide synthesis by keeping the phenolic side chain protected during handling, coupling, and workup steps. In practice, this reduces variability associated with phenol oxidation and side reactions that can complicate crude composition and downstream purification by chromatography. Analytical and synthesis teams preparing research-grade peptides for structure-activity relationship studies often select this protected tyrosine derivative when they need cleaner reaction profiles and more predictable chromatographic behavior, particularly for longer sequences or for batches where reproducibility across multiple syntheses is a priority.
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