Boc-D-Tyr(2,6-Cl2-Bzl)-OH is a Boc-protected D-tyrosine derivative in which the tyrosine phenolic side chain is benzylated with a 2,6-dichlorobenzyl group, yielding an amino acid bearing an aromatic, halogenated ether substituent. The molecule contains a Boc carbamate protecting the α-amino group and a free carboxylic acid functionality, while the side chain oxygen is masked as a benzyl ether to control chemoselectivity during peptide bond formation and subsequent deprotection steps. As a protected amino acid building block, it is used in peptide synthesis workflows to introduce a tyrosine analogue with a sterically and electronically modified phenolic environment for structure-activity studies, protein fragment preparation, and analytical method development.
CAT No: CP25992
CAS No:69541-62-4
Synonyms/Alias:69541-62-4;BOC-D-TYR(2,6-CL2-BZL)-OH;C21H23Cl2NO5;AmbotzBAA1380;BOC-D-TYR-OH;SCHEMBL4417313;MolPort-008-267-421;ZINC1576317;Boc-D-Tyr(2,6-dichloro-Bzl)-OH;6353AH;KM1279
Chemical Name:N-alpha-t-Butyloxycarbonyl-O-(2,6-dichlorobenzyl)-D-tyrosine
Boc-D-Tyr(2,6-Cl2-Bzl)-OH is a protected D-configured tyrosine derivative designed for peptide and peptidomimetic synthesis, featuring a Boc-protected amino group and a benzyl-protected phenolic side chain substituted with two chlorine atoms at the 2 and 6 positions. The 2,6-dichloro-benzyl protection pattern provides steric shielding of the phenolic oxygen, supporting controlled side-chain handling during assembly of complex sequences. This reagent is commonly used by peptide chemists and medicinal chemistry teams when a tyrosine residue with a protected, electronically tuned side chain is required for downstream coupling, fragment condensation, or selective deprotection workflows.
1. Solid-Phase Peptide Synthesis
Boc-D-Tyr(2,6-Cl2-Bzl)-OH is used as a protected amino acid building block for solid-phase peptide synthesis workflows where incorporation of a D-tyrosine residue is desired for stereochemical control, protease resistance studies, or conformational design. The Boc amino protection and phenolic benzyl protection enable routine coupling strategies while keeping the tyrosine oxygen masked throughout chain assembly. Medicinal chemistry groups preparing D-amino acid-containing peptide libraries and custom peptide sequences rely on this type of protected derivative to maintain side-chain integrity during iterative deprotection/coupling cycles and to minimize unwanted side reactions from the phenolic functionality.
2. Peptidomimetic Fragment Coupling
Boc-D-Tyr(2,6-Cl2-Bzl)-OH is well suited to solution-phase or fragment condensation approaches used in peptidomimetic development, where controlled assembly of tyrosine-containing segments is required before final global deprotection. The protected phenolic oxygen (as a 2,6-dichloro benzyl ether/benzyl-protected form) helps prevent premature side-chain participation during coupling and allows chemists to sequence deprotection steps to match the overall synthetic plan. Teams developing non-natural peptide analogs for chemical biology studies and structure-activity relationship work often select this reagent when a tyrosine-like aromatic handle must remain protected while other functional groups in the fragment are manipulated.
3. Pharmaceutical Intermediate Development
Boc-D-Tyr(2,6-Cl2-Bzl)-OH is also used as a pharmaceutical intermediate building block in the preparation of protected D-tyrosine derivatives and related advanced intermediates for downstream synthesis of peptide-based candidates or research materials. The combination of Boc protection and 2,6-dichloro benzyl side-chain protection provides a practical protection strategy for handling an otherwise reactive phenolic group during intermediate elaboration. Process chemistry and intermediate development scientists value this protected form when they need reliable, isolable intermediates that support stepwise manufacturing of complex, tyrosine-containing structures without uncontrolled phenol reactivity.
4. Stereodefined Tyrosine Analog Synthesis
Boc-D-Tyr(2,6-Cl2-Bzl)-OH supports stereodefined synthesis of tyrosine analogs where D-configuration at the backbone position is a deliberate design variable. Researchers in peptide engineering and chemical biology frequently incorporate D-amino acids to probe structure-function relationships, assess stability trends in proteolysis models, or generate stereochemically constrained analogs for binding studies. The protected phenolic side chain ensures that the aromatic oxygen does not interfere during the early stages of analog construction, allowing later-stage conversion to the desired functional state as part of a controlled synthetic sequence.
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