Boc-Ala-aldehyde is a protected alanine-derived amino acid aldehyde in which the amino group is masked as a Boc (tert-butoxycarbonyl) carbamate and the side chain corresponds to the alanine methyl substituent. The molecule contains a free aldehyde functionality along with the Boc-protected amino group and a carboxyl-derived carbonyl equivalent consistent with an amino acid aldehyde framework, with stereochemistry at the alanine center implied only insofar as the starting alanine configuration is carried through. In peptide and amino-acid chemistry workflows, it is employed as a carbonyl-bearing alanine building block for constructing larger peptidic or amino-acid-derived structures and for preparing aldehyde-reactive intermediates used in chemical biology labeling and conjugation strategies.
CAT No: CP27482
CAS No:79069-50-4
Synonyms/Alias:Boc-L-alaninal;79069-50-4;(S)-tert-Butyl(1-oxopropan-2-yl)carbamate;Boc-Ala-Aldehyde;Boc-L-alaninealdehyde;CHEMBL94727;(S)-tert-butyl1-oxopropan-2-ylcarbamate;N-Boc-2(S)-2-aminopropanal;(1-Methyl-2-oxo-ethyl)-carbamicacidtert-butylester;AC1Q29KO;AC1Q29KP;B1403_SIGMA;SCHEMBL327825;(S)-(1-METHYL-2-OXO-ETHYL)-CARBAMICACIDTERT-BUTYLESTER;CTK5E6419;MolPort-003-741-801;OEQRZPWMXXJEKU-LURJTMIESA-N;ZINC2516824;ANW-43421;BDBM50137807;KM1953;MFCD00143786;tert-butyl(S)-1-formylethylcarbamate;AKOS005146520;AKOS015840143
Boc-Ala-aldehyde is an amino acid aldehyde derivative built on the alanine side chain, bearing an N-Boc protecting group and a terminal aldehyde functionality that enables further derivatization. This protected aldehyde form is widely handled as a reactive building block for constructing peptide-related intermediates and for assembling carbonyl-containing fragments where controlled reactivity is required. In synthetic workflows, the Boc group provides compatibility with protected-amino-acid chemistry while the aldehyde serves as a key electrophile for downstream coupling, reductive amination, or conversion to other carbonyl derivatives.
1. Peptide Intermediate Building
Boc-Ala-aldehyde is used by peptide synthesis and custom peptide manufacturing teams as a practical intermediate for preparing alanine-containing segments that require a protected amino terminus alongside a reactive aldehyde handle. The N-Boc protection supports standard protected-amino-acid handling during intermediate assembly, while the aldehyde enables transformation into downstream functionalities needed for segment condensation strategies or for generating tailored carbonyl-containing linkers. This makes the material particularly relevant when a workflow needs an alanine-derived carbonyl synthon rather than a fully activated carboxylic acid derivative.
2. Aldehyde-Derived Coupling Chemistry
Boc-Ala-aldehyde is commonly selected in medicinal chemistry and chemical biology synthesis for building carbon-nitrogen or carbon-carbon frameworks starting from a Boc-protected amino aldehyde. The aldehyde group provides a convenient electrophilic site for forming substituted amines via reductive amination routes or for generating further carbonyl derivatives through standard aldehyde reactivity, while the Boc group helps maintain the amino functionality in a protected, non-interfering state during derivatization. Researchers developing peptidomimetic scaffolds, linker chemistries, or intermediate libraries often favor this reagent because it combines amino protection with a single, well-defined reactive carbonyl.
3. Pharmaceutical Intermediate Development
Boc-Ala-aldehyde is applied in pharmaceutical intermediate development where alanine-based, protected amino aldehydes are required as branching points for downstream synthesis. Process and synthesis teams use it to access carbonyl-bearing intermediates that can be converted into various functionalized derivatives needed for structure-activity relationship (SAR) exploration or for assembling more complex molecules with controlled functional group placement. The Boc-protected amino group supports robust handling through multi-step sequences, while the aldehyde enables rapid diversification into multiple intermediate classes used downstream in specialty chemical manufacturing.
4. Chiral Building Block Diversification
Boc-Ala-aldehyde is frequently used in chiral synthesis and stereochemically controlled intermediate preparation when an alanine-derived aldehyde motif is needed as a starting point for further stereodefining transformations. Synthetic chemists value the combination of a protected amino group and an aldehyde electrophile because it allows selective functionalization without immediately exposing the amino functionality to conditions that could lead to side reactions. This approach supports the generation of stereochemically relevant intermediates used in the preparation of constrained peptidomimetic fragments and other chiral, carbonyl-functional building blocks.
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