Boc-D-Thr(tBu)-OH is a protected amino acid derivative based on D-threonine, featuring a side chain bearing a hydroxyl group and a methyl substituent on the β-carbon. The amino group is protected as a Boc (tert-butoxycarbonyl) carbamate, while the threonine side-chain hydroxyl is protected as a tert-butyl ether (tBu), yielding a molecule with both a carboxyl functional group and protected amine/oxygen functionalities. This protected analogue is used as a building block in peptide synthesis and related stepwise coupling strategies, where the Boc group and the tert-butyl side-chain protection help control chemoselectivity during assembly of peptide or peptide-like structures.
CAT No: CP26698
CAS No:201217-86-9
Synonyms/Alias:201217-86-9;BOC-D-THR(TBU)-OH;Boc-O-tert-butyl-D-threonine;(2R,3S)-3-(tert-Butoxy)-2-((tert-butoxycarbonyl)amino)butanoicacid;BOC-D-THR-OH;SCHEMBL8222608;CTK8B3884;MolPort-020-004-757;ZINC2560692;ANW-43373;CB-358;AKOS024259129;AJ-40625;AK-81069;RT-011792;FT-0697956;ST24034012;V4162;K-5882
Boc-D-Thr(tBu)-OH is a protected D-threonine derivative bearing a Boc-protected alpha-amino group and a tert-butyl-protected side-chain hydroxyl, providing orthogonal stability during peptide assembly and downstream transformations. This amino acid building block is commonly selected when D-configuration at threonine is required and when the side-chain alcohol must remain protected to prevent undesired reactions during coupling and deprotection steps. The protected functionality makes it a practical component for constructing stereochemically defined peptides and peptide-based intermediates in research and development workflows.
1. D-Thr Peptide Building Block
Boc-D-Thr(tBu)-OH is used as an amino acid building block for peptide synthesis workflows that require incorporation of D-threonine with the side-chain hydroxyl protected as a tert-butyl ether. Peptide chemists rely on this protection pattern to maintain chemoselectivity during sequential couplings, particularly when assembling longer sequences or when additional functional groups in neighboring residues must be preserved. The Boc-protected amino group supports its use in protected-amino-acid strategies for generating stereochemically defined peptide segments, including D-amino-acid-containing analogs used to probe sequence effects, stability, and structure.
2. Stereodefined Peptide Analog Development
Boc-D-Thr(tBu)-OH is frequently selected in medicinal chemistry and chemical biology programs developing stereochemically defined peptide analogs where D-threonine placement is used to control local backbone geometry and side-chain presentation. Researchers preparing D-amino-acid-containing fragments often need the threonine hydroxyl protected throughout assembly to avoid side reactions that can occur when free alcohols are present under peptide coupling and deprotection conditions. This makes the reagent useful for producing well-defined peptide intermediates that can later be processed to expose the threonine side-chain functionality for subsequent derivatization or for final peptide characterization.
3. Protected Segment Intermediate Synthesis
Boc-D-Thr(tBu)-OH serves as a protected segment intermediate component for custom peptide manufacturing and research-scale synthesis where controlled deprotection sequencing is important. In workflows that generate partially protected peptide fragments for later ligation or segment condensation, maintaining the threonine side-chain as a tert-butyl-protected group helps prevent premature alcohol reactivity and supports consistent downstream handling. The Boc protection on the amino functionality also aligns with strategies that require stepwise unmasking of reactive sites to enable controlled assembly of complex peptide architectures.
4. Side-Chain Functionalization Precursor
Boc-D-Thr(tBu)-OH is applied as a precursor for peptide derivatives where the threonine side-chain hydroxyl must be introduced in a controlled manner after peptide assembly. By keeping the side-chain protected during synthesis, researchers can first build the peptide framework and then later unmask the hydroxyl to support subsequent derivatization steps such as conversion to activated forms for further coupling chemistry or attachment of functional substituents. This approach is particularly valuable when the target derivative requires precise positioning of the threonine alcohol for downstream conjugation chemistry or for generating structure-defined analogs used in chemical biology and materials-oriented peptide studies.
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