(R)-N-Boc-α-Allylalanine Ethyl ester is a protected, esterified amino acid derivative featuring an α-amino acid backbone with an allyl-substituted alanine side chain and an ethyl ester at the carboxyl terminus. The amino group is protected as an N-Boc carbamate, and the (R) stereochemistry at the α-carbon is specified, while the side-chain allyl functionality provides a carbon-carbon double bond that can participate in subsequent derivatization. In peptide and amino-acid chemistry workflows, this compound is employed as a protected building block and precursor for incorporating the allyl-bearing residue into larger peptide frameworks or for generating allyl-functional analogues used in structure-activity studies, chemical biology conjugation strategies, and analytical method development.
CAT No: CP27634
CAS No:1263046-12-3
Chemical Name:Boc-α-Me-D-Gly(Allyl)-Oet
(R)-N-Boc-α-Allylalanine Ethyl ester is a chiral, N-Boc-protected amino acid ester featuring an allyl side chain that provides a convenient handle for downstream functionalization while maintaining stereochemical integrity. As an amino acid derivative, it is commonly handled as a protected building block for peptide and peptidomimetic assembly, where the Boc group supports controlled coupling chemistry and the ethyl ester serves as a protected carboxyl functionality during synthesis. The allyl substituent enables selective transformation into more functional motifs for medicinal chemistry and materials-oriented linker design.
1. Peptidomimetic Building Blocks
(R)-N-Boc-α-Allylalanine Ethyl ester is frequently used by medicinal chemistry and peptide-chemistry groups to prepare peptidomimetic scaffolds and modified amino acid residues that retain a defined stereocenter. The N-Boc protection supports standard peptide-coupling workflows to incorporate the residue into short sequences or larger constructs, while the ethyl ester form is convenient during intermediate stages where carboxyl activation and later conversion are required. The allyl side chain is particularly useful for introducing diversity after assembly, enabling subsequent derivatization steps that broaden structure-activity relationship exploration without changing the backbone stereochemistry.
2. Side-Chain Functionalization Intermediates
(R)-N-Boc-α-Allylalanine Ethyl ester is a practical intermediate for building functionalized alanine analogs where the allyl group is used as a synthetic "growth point" toward higher-value side-chain chemistries. Research teams in pharmaceutical intermediate development and chemical biology often choose this scaffold because it combines a protected amino functionality with a chemically modifiable side chain, allowing the allyl moiety to be converted into alternative substituents in later stages while keeping the N-protection and ester as controllable protecting elements. This approach is commonly applied when preparing libraries of modified amino acids for SAR studies, receptor-binding analogs, or enzyme-substrate analogs.
3. Stereodefined Chiral Synthesis
(R)-N-Boc-α-Allylalanine Ethyl ester is used in chiral synthesis programs that require stereodefined amino acid derivatives as starting points for downstream asymmetric or stereospecific transformations. The (R) configuration makes it a reliable input for constructing chiral centers in peptidomimetic and medicinal chemistry intermediates, where maintaining stereochemical fidelity is essential for reproducible structure-property relationships. By using a protected, esterified form, synthetic workflows can proceed through coupling/derivatization sequences with reduced risk of premature functional group interference, supporting efficient preparation of enantiopure intermediates for custom synthesis and development chemistry.
4. Protected Amino Acid Derivatization
(R)-N-Boc-α-Allylalanine Ethyl ester is well suited for stepwise derivatization strategies in custom peptide manufacturing research and specialty chemical development, where amino acid protection and ester masking are used to control reactivity across multiple synthetic operations. The Boc-protected nitrogen supports selective handling during intermediate transformations, while the ethyl ester provides a stable carboxyl equivalent for staged conversion to acids, amides, or activated derivatives in later steps. Laboratories preparing modified amino acid building blocks for incorporation into larger peptide-like molecules often rely on this format to streamline intermediate management while preserving the allyl side chain for targeted downstream conversion.
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