Boc-L-leucinol is a Boc-protected amino alcohol derived from L-leucine, featuring a branched isobutyl side chain and a hydroxymethyl group that converts the original carboxyl-bearing amino acid into an alcohol functionality. The molecule contains a carbamate-protected amino group (Boc) and a free alcohol, with stereochemistry consistent with the L-leucine origin indicated by the name. As a protected amino alcohol building block, it is used in peptide and peptidomimetic synthesis and in the preparation of amino-alcohol-containing derivatives for structure-activity studies, linker design, and chemical labeling workflows where controlled amine reactivity is required.
CAT No: CP27503
CAS No:82010-31-9
Synonyms/Alias:Boc-L-leucinol;N-BOC-L-Leucinol;82010-31-9;Boc-Leucinol;Tert-ButylN-[(2S)-1-Hydroxy-4-Methylpentan-2-Yl]Carbamate;ST50825678;(S)-(-)-2-(Boc-Amino)-4-methyl-1-pentanol;Boc-Leu-ol;N-BocL-Leucinol;ZINC02555022;PubChem12195;AC1Q1O8W;L-Leucinol,N-BOCprotected;SCHEMBL272780;ARK052;CTK3J1835;N-(t-butoxycarbonyl)-L-leucinol;LQTMEOSBXTVYRM-VIFPVBQESA-N;MolPort-001-793-338;ACT04162;ZINC2555022;ANW-37491;CB-011;MFCD00076950;AKOS015841822
Boc-L-leucinol is a Boc-protected, L-configured leucine-derived amino alcohol featuring a secondary alcohol on the side chain. As a protected amino acid derivative, it is commonly used as a chiral building block for peptide and peptidomimetic synthesis workflows where an amino-alcohol functionality is required for downstream coupling, stereochemical control, or incorporation into constrained motifs. The Boc group provides a stable, masked amine handle that can be revealed under standard peptide-intermediate processing conditions to enable formation of amide or related linkages in research-grade chemical manufacturing.
1. Peptidomimetic Building Block
Boc-L-leucinol is frequently selected by medicinal chemistry and chemical biology groups building peptidomimetic scaffolds that incorporate an amino alcohol in place of a canonical amino acid side chain. Its L-stereochemistry and branched leucine-derived carbon framework support the creation of constrained, stereodefined analogs used in structure-activity relationship studies and receptor/ligand binding probe development. The Boc-protected amine allows controlled assembly into larger fragments during custom synthesis, including the preparation of side-chain-modified peptides and peptide-like inhibitors where alcohol functionality is used to tune hydrogen-bonding patterns and local conformation.
2. Protected Chiral Intermediate Synthesis
Boc-L-leucinol serves as a practical chiral intermediate for pharmaceutical intermediate development and specialty chemical manufacturing, particularly when a leucine-derived amino alcohol is needed as an entry point to more complex heterocycles, amide-linked fragments, or protected alcohol derivatives. Process chemists and synthesis teams use the Boc-protected amine to manage chemoselectivity during multistep sequences, while the free alcohol provides a functional handle for further derivatization to ethers, esters, or other downstream intermediates used in library synthesis. This combination of masked nitrogen and unmasked hydroxyl makes the compound a convenient stereodefined precursor for generating diversified small-molecule building blocks.
3. Amide-Linked Fragment Coupling
Boc-L-leucinol is commonly used in custom peptide synthesis and solution-phase fragment assembly when an amino-alcohol-containing residue is desired as part of a larger amide-linked construct. Researchers preparing modified peptides, peptidomimetics, or backbone/side-chain analogs rely on the Boc group to keep the amine protected during fragment handling and coupling steps, then to enable subsequent formation of amide bonds to carboxylic acid partners in the final assembly workflow. The leucine-derived hydrophobic side chain and the stereodefined carbon bearing the hydroxyl group help introduce a distinct physicochemical profile into the resulting conjugates, which is valuable for designing structure-defined chemical probes and synthetic analogs for biochemical characterization.
4. Chiral Derivatization and Analytical Standards
Boc-L-leucinol is also used in analytical and method-development contexts where a stereochemically defined amino alcohol reference material is needed for derivatization-based workflows and chiral assessment strategies. Laboratories developing LC/GC methods, stereochemical confirmation procedures, or derivatization reagents for amino-alcohol motifs may employ this Boc-protected intermediate as a stable, well-defined starting point. The presence of both a protected amine and a hydroxyl group supports controlled derivatization chemistry, enabling reproducible formation of downstream analytical derivatives used to support identification, purity checks, and stereochemical verification during research synthesis and intermediate qualification.
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