Boc-L-Ala-CHN2 is a protected amino acid derivative in which L-alanine is functionalized at the amino group with a Boc (tert-butoxycarbonyl) protecting group and at the carboxyl terminus with a diazomethyl (CHN2) functionality. The molecule therefore contains a Boc-protected α-amino group and an ester-like carboxyl-derived diazo unit, with the stereochemistry indicated as L at the α-carbon and the side chain being the methyl group characteristic of alanine. In synthesis and chemical biology workflows, this CHN2 handle can be used as a diazo functional group precursor for constructing more complex amino acid and peptide-related intermediates, including routes where diazo chemistry is employed for subsequent functionalization under controlled conditions.
CAT No: CP25985
CAS No:67919-80-6
Chemical Name:N-alpha-t-Butyloxycarbonyl-L-alaninyl-diazomethane, (3S)-3-Boc-amino-1-diazo-2-butanone
Boc-L-Ala-CHN2 is a Boc-protected L-alanine derivative bearing a diazomethyl (CHN2) functionality, providing a protected amino acid backbone combined with a reactive diazo group for downstream chemical transformations. This structure is commonly used in synthetic workflows where the Boc group enables controlled handling of the amino acid stereocenter while the diazo functionality serves as a versatile intermediate for building substituted carbonyl and related motifs. In research and development settings, Boc-L-Ala-CHN2 is selected when a diazo-bearing alanine equivalent is needed as a reagent for preparing specialized amino acid derivatives, labeled or functionalized fragments, and peptide-related intermediates.
1. Diazomethyl Alanine Intermediates
Boc-L-Ala-CHN2 is used as a diazomethyl alanine building block in medicinal chemistry and pharmaceutical intermediate development, where the diazo group provides access to substituted carbonyl-containing fragments and other diazo-derived products under conditions chosen by the synthetic route. Process and R&D teams value the Boc-protected amino acid framework because it maintains the amino acid functionality in a protected, non-interfering form during diazo-related transformations, enabling sequential assembly of more complex intermediates. This reagent is particularly relevant when an alanine-derived stereocenter must be carried through to a later-stage functionalized scaffold.
2. Peptide Fragment Derivatization
Boc-L-Ala-CHN2 serves as a specialized intermediate for preparing alanine-containing peptide fragments and modified amino acid units used in custom peptide synthesis and peptide library workflows. In these applications, the Boc protection supports controlled downstream coupling or conversion to other protected forms, while the diazo functionality allows incorporation of a chemically distinct handle that can be transformed into the desired linkage or substituent pattern before final peptide assembly. Peptide chemists and contract peptide manufacturers often select diazo-bearing amino acid derivatives when they need a defined, stereochemically consistent alanine unit that can be diversified beyond standard protected amino acids.
3. Carbonyl-Directed Scaffold Building
Boc-L-Ala-CHN2 is applied in synthetic chemistry for constructing carbonyl-directed scaffolds via diazo chemistry, supporting the generation of substituted intermediates that can be further elaborated into heterocycles, acyl derivatives, or functionalized side-chain analogs. Medicinal chemistry groups and specialty chemical developers use this reagent when they require a diazo-bearing amino acid equivalent that integrates stereochemical integrity from the alanine backbone with a reactive diazo moiety for rapid diversification. The Boc group helps keep the amino acid nitrogen protected, reducing unwanted side reactions and improving compatibility with multi-step synthetic sequences where the diazo functionality is the key transformation point.
4. Specialty Isotope-Labeling Precursors
Boc-L-Ala-CHN2 is also used as a specialized precursor in isotope-labeling and labeling-method development when diazo-functionalized alanine derivatives are required as intermediates for downstream incorporation into labeled fragments. Analytical and chemical biology laboratories may employ this type of reagent to generate labeled or derivatized alanine-containing motifs that are then used for method development, reference material preparation, or tracing studies in broader synthetic campaigns. The combination of a protected amino acid backbone with a diazo group makes it useful for routes where the diazo functionality must be installed or manipulated prior to introducing labeling or finalizing the labeled target building block.
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