(S)-α-Allylglycine ethyl ester p-toluenesulfonate contains an α-amino acid backbone bearing an allyl side chain, with the amino acid carboxyl group converted to an ethyl ester and the amino functionality present as a p-toluenesulfonate salt; the (S) stereochemical designation specifies the configuration at the α-carbon. The molecule therefore features an esterified carboxyl group and a sulfonate counterion associated with the amino group, providing a protected/derivatized form that can reduce free zwitterionic behavior and support controlled handling during synthesis. As a peptide-building amino acid ester and salt, it is employed as a precursor for preparing allyl-containing amino acid derivatives and for incorporation of the allylglycine motif into larger peptide or peptidomimetic structures in solution-phase or solid-phase synthetic workflows.
CAT No: CP27635
CAS No:1231709-21-9
Synonyms/Alias:(S)-alpha-Allylglycine ethyl ester p-toluenesulfonate;
(S)-α-Allylglycine ethyl ester p-toluenesulfonate is a chiral allylglycine derivative supplied as an ethyl ester salt with p-toluenesulfonate, combining a stereodefined amino acid backbone with an allyl side chain for downstream functionalization. The (S)-configuration supports use in stereochemically controlled synthesis, while the ester and salt form provide a practical handle for coupling chemistry and intermediate preparation. In research and development workflows, it is commonly selected as an amino acid building block for constructing peptidomimetic frameworks and for introducing allyl functionality into larger molecules.
1. Peptidomimetic Building Block
(S)-α-Allylglycine ethyl ester p-toluenesulfonate is used as a stereodefined amino acid building block in peptidomimetic and constrained peptide-like scaffold synthesis, where the allyl side chain serves as a convenient functional group for later derivatization. Medicinal chemistry groups and custom synthesis providers often incorporate allylglycine motifs to probe structure-activity relationships, generate analog libraries, and access analogs bearing unsaturated substituents without changing the stereochemical outcome of the chiral center. The ethyl ester form is particularly useful for preparing activated derivatives or for sequential assembly strategies that require a protected carboxyl equivalent during fragment coupling.
2. Allyl Functionalization Intermediates
(S)-α-Allylglycine ethyl ester p-toluenesulfonate is frequently employed as an intermediate precursor for allyl-based transformations, enabling conversion of the side-chain alkene into downstream functionalities used in chemical biology probe development and materials-oriented linker design. Organic synthesis teams use the allyl handle to access a range of functionalized products through established alkene modification workflows, while the amino acid-derived backbone maintains a defined spatial relationship between the stereocenter and the reactive side chain. The p-toluenesulfonate salt form also supports handling and consistent reactivity during multistep intermediate preparation, which is valuable in scale-up and library synthesis settings.
3. Stereoselective Chiral Synthesis
(S)-α-Allylglycine ethyl ester p-toluenesulfonate is selected when a chiral amino acid fragment with a defined (S)-configuration is required for stereoselective construction of larger molecules. Process development chemists and pharmaceutical intermediate manufacturers use this reagent to introduce a chiral center early in a synthetic sequence, improving control over stereochemical integrity across subsequent steps that build complexity from amino acid-derived fragments. The combination of a chiral α-center with an allyl side chain makes it a practical starting point for generating stereochemically consistent analogs, particularly when downstream steps depend on maintaining the relative configuration of the amino acid motif.
4. Pharmaceutical Intermediate Development
(S)-α-Allylglycine ethyl ester p-toluenesulfonate is used in the development of specialized pharmaceutical intermediates and advanced building blocks for medicinal chemistry programs, especially when an allylglycine-derived unit is needed as a modular fragment. R&D teams incorporate this compound into synthetic routes that require an amino acid-derived backbone with an ester functionality and a modifiable alkene side chain, supporting the rapid generation of structural variants for lead optimization. The reagent's salt and ester format aligns with typical intermediate handling practices in custom synthesis and process chemistry, where predictable physical form and compatibility with coupling/derivatization steps are important for workflow efficiency.
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