L-beta-Phenyllactic acid-OMe is a methyl ester derivative of beta-phenyllactic acid, featuring a secondary hydroxy-substituted propanoate backbone bearing a benzyl side chain and an O-methyl ester at the carboxyl position. The molecule contains a free hydroxyl group on the beta carbon and an esterified carboxyl group, with stereochemistry indicated by the "L-" prefix while the beta-hydroxy configuration is reflected in the "beta" designation. As an amino-acid-like building block and protected carboxyl equivalent, it is used in synthetic chemistry and chemical biology workflows to prepare further functionalized beta-hydroxy acid derivatives, generate conjugation-ready intermediates, or support structure-activity and labeling studies where ester-stabilized hydroxy acid motifs are required.
CAT No: CP26345
CAS No:13673-95-5
Synonyms/Alias:13673-95-5;(S)-methyl2-hydroxy-3-phenylpropanoate;Methyl-(2S)-2-hydroxy-3-phenylpropanoate;methyl(2S)-2-hydroxy-3-phenylpropanoate;MethylL-3-phenyllactate;Methyl(S)-2-hydroxy-3-phenylpropionate;3-phenyllacticacidmethylester;PubChem6055;AC1NRCMM;L-3-Phenyllacticacid-OMe;KSC493S5F;68193_ALDRICH;SCHEMBL3980617;68193_FLUKA;CTK3J3952;MolPort-003-935-640;NMPPJJIBQQCOOI-VIFPVBQESA-N;ACT04288;ZINC2390922;ANW-42533;CP-211;FD1247;MFCD00038224;ZINC02390922;AKOS005067766
L-beta-Phenyllactic acid-OMe is a chiral hydroxy ester derived from L-beta-phenyllactic acid, featuring a stereogenic center at the beta-carbon, a benzylic phenyl substituent, and an esterified carboxyl group as the methyl ester (OMe). The molecule bears a secondary alcohol that can participate in esterification, ether formation, oxidation to a keto functionality, or conversion to leaving groups for substitution chemistry. The chiral arrangement of the beta-hydroxy and the phenyl-bearing stereocenter makes it a practical stereodefined intermediate for downstream amino acid and peptidomimetic-related scaffolds, where controlled stereochemistry is required for binding-site mimicry or conformational bias. The ester and alcohol combination also supports protection-group strategies and selective functional group transformations that are compatible with multi-step synthetic sequences.
1. Chiral Building Block Synthesis
L-beta-Phenyllactic acid-OMe is applied in chiral synthesis workflows where a stereodefined beta-hydroxy ester serves as a controlled precursor for building block diversification. The methyl ester provides a handle for selective hydrolysis, transesterification, or conversion to activated carboxy derivatives, while the secondary alcohol enables derivatization to ethers or carbonate/ester protecting-group analogs. The benzylic phenyl substituent and the L-configuration at the beta-carbon support stereospecific transformations that preserve or translate chirality into downstream intermediates. The resulting chiral intermediates can be used to construct stereochemically defined fragments for fine chemical synthesis and stereocontrolled route development.
2. Peptidomimetic Fragment Construction
L-beta-Phenyllactic acid-OMe can be employed as an amino acid-mimicking precursor in peptidomimetic construction, particularly when beta-hydroxy motifs are used to emulate backbone oxygenation patterns or side-chain conformational effects. The beta-hydroxy ester functionality can be converted into carboxylate equivalents for coupling chemistry, while the alcohol can be transformed into leaving groups or protected forms to enable selective functionalization without racemization at the stereocenter. The phenyl-bearing chiral center can be mapped into aromatic side-chain surrogates used in structure-activity relationship studies of peptide-like ligands. Downstream derivatives may include hydroxy-containing amide-forming intermediates and scaffold fragments that integrate into larger peptide analogs and constrained mimetics.
3. Chemical Manufacturing Intermediates
L-beta-Phenyllactic acid-OMe is suitable for industrial intermediate preparation in process chemistry where chiral hydroxy esters are used to feed downstream functional group interconversions on manufacturing timelines. The methyl ester can be hydrolyzed to the corresponding acid or converted into activated carboxy intermediates for further synthesis, while the secondary alcohol can be oxidized or derivatized to modulate reactivity and downstream selectivity. The presence of a single stereocenter supports consistent stereochemical outcomes across batch-to-batch synthesis, which is relevant for scale-up of chiral fine chemicals. The compound can therefore function as a practical chiral feedstock for specialty chemical production routes that require controlled conversion of ester and alcohol functionalities into more reactive or more stable forms.
4. Stereoselective Functional Group Transformations
L-beta-Phenyllactic acid-OMe is used in synthetic organic chemistry as a stereodefined platform for sequential functional group transformation, leveraging the orthogonal reactivity of the ester and secondary alcohol. The alcohol can be protected as an ether or carbonate to enable selective ester manipulation, while the ester can be selectively modified to generate carboxyl-derivative intermediates for coupling or further elaboration. Oxidation of the secondary alcohol to a keto functionality can introduce carbonyl chemistry for subsequent nucleophilic addition or reductive amination, while maintaining the stereochemical information embedded in the beta-carbon. The resulting functionalized products can serve as intermediates for heterocycle synthesis, aromatic-substituted chiral fragments, and other downstream stereocontrolled syntheses.
5. Analytical Reference and Method Development
L-beta-Phenyllactic acid-OMe can be applied in analytical research and method development where a chiral hydroxy ester reference material supports stereochemical assignment and impurity profiling. The combination of an ester and a secondary alcohol provides distinct chromatographic and spectroscopic signatures that can be used to track conversion, monitor stereochemical integrity, and validate derivatization strategies in chiral analysis workflows. The L-configuration and benzylic phenyl group can help calibrate enantioselective separation methods and support identification of structurally related beta-hydroxy ester impurities. Analytical-grade derivatives prepared from this scaffold can also serve as standards for quality control of upstream chiral synthesis intermediates and for downstream process monitoring in applied chemical manufacturing.
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