L-Aspartic acid dibenzyl ester tosylate is a protected amino acid derivative derived from L-aspartic acid, featuring the side-chain carboxyl group converted to a dibenzyl ester while the amino acid framework is maintained as a functional precursor for further transformations. The molecule contains an amino group and a carboxylate functionality masked as benzyl esters, and the "tosylate" component indicates an additional tosyl-protected leaving group or sulfonate-derived protection that can modulate chemoselectivity during stepwise synthesis. In peptide-related and synthetic chemistry contexts, this compound is employed as a protected aspartate building block to control reactivity of the carboxyl groups and to support preparation of aspartyl-containing intermediates, conjugates, and other structurally defined amino acid derivatives.
CAT No: CP00450
CAS No:2886-33-1
Synonyms/Alias:2886-33-1;h-asp(obzl)-obzltosoh;H-Asp(OBzl)-OBzl.TosOH;(s)-dibenzyl2-aminosuccinate4-methylbenzenesulfonate;l-asparticaciddibenzylestertosylate;SBB058098;L-Asparticaciddibenzylesterp-toluenesulfonatesalt;H-Asp(OBzl)-OBzl.Tos;L-Asparticaciddibenzylesterp-toluenesulfonate;H-Asp(OBzl)-OBzlinvertedexclamationmarkcurrencyTosOH;L-Asparticaciddibenzylester4-toluenesulfonate;diphenylmethyl(2S)-2-aminobutane-1,4-dioate,4-methylbenzenesulfonicacid;PubChem18995;Asp(OBzl)-OBzl?TosOH;H-Asp(OBzl)-OBzlosOH;AC1MDB4E;Maybridge1_003976;H-Asp(OBzl)-OBzl.Tos-OH;459887_ALDRICH;C25H27NO7S;SCHEMBL5396953;Jsp005508;CTK1A1883;HMS552M16;HLMUYZYLPUHSNV-NTISSMGPSA-N
L-Aspartic acid dibenzyl ester tosylate is an L-aspartate-derived amino acid ester intermediate in which the amino acid backbone is converted to a dibenzyl ester and the side-chain functionality is present as a tosylate leaving group, enabling controlled downstream transformations. The molecule retains the stereogenic center of L-aspartic acid, and the benzyl ester groups provide acid-labile protection that is compatible with peptide-coupling workflows after deprotection. The tosylate on the side-chain oxygen introduces a robust, non-nucleophilic handle that can be displaced under nucleophilic substitution conditions to install diverse side-chain motifs. The combination of protected carboxylate ester groups and a reactive sulfonate leaving group supports both stereochemically defined intermediate construction and functionalized amino acid derivative synthesis for synthetic and biochemical research.
1. Protected Amino Acid Synthesis
L-Aspartic acid dibenzyl ester tosylate is used as a protected amino acid intermediate for building stereodefined aspartate derivatives in protected amino acid synthesis and peptide building block preparation. The dibenzyl ester functionality masks the α- and side-chain carboxylates during coupling chemistry, while the tosylate provides a controlled transformation point for side-chain modification without prematurely exposing polar acid groups. Side-chain functionalization via tosylate displacement can generate aspartate analogs bearing nucleophilic substituents suitable for subsequent ester hydrolysis, amide formation, or further protection/deprotection planning. L-Aspartic acid dibenzyl ester tosylate therefore supports stepwise synthesis of functionalized aspartate building blocks that feed into peptide coupling chemistry and downstream scaffold diversification.
2. Side-Chain Functionalization
L-Aspartic acid dibenzyl ester tosylate is applied in side-chain functionalization strategies where the tosylate leaving group enables installation of heteroatom-containing substituents onto the aspartate framework. The L-configuration preserves stereochemical integrity at the α-carbon, while the ester-protected carboxylates reduce competing side reactions during nucleophile introduction at the side-chain position. The sulfonate leaving group can be used to generate derivatives that carry protected alcohols, amines, or other nucleophile-derived substituents, which can then be converted into amide or ester linkages for incorporation into larger molecules. L-Aspartic acid dibenzyl ester tosylate thereby serves as a practical chiral intermediate for producing functionalized amino acid derivatives used in synthetic organic chemistry and peptide analog construction.
3. Peptide Coupling Chemistry
L-Aspartic acid dibenzyl ester tosylate is utilized in peptide synthesis planning where protected aspartate esters act as coupling-compatible building blocks after appropriate deprotection and activation steps. The dibenzyl ester groups provide a protecting-group platform that can be removed under hydrogenolysis-compatible conditions to reveal carboxylates for subsequent activation to activated esters or acid derivatives. The tosylate functionality can be retained for controlled timing of side-chain elaboration, allowing the synthesis route to separate side-chain modification from backbone coupling. L-Aspartic acid dibenzyl ester tosylate supports the preparation of aspartate-containing peptide fragments and peptidomimetic precursors, enabling stereochemically defined incorporation of modified side chains into peptide sequences.
4. Chemical Biology Probes
L-Aspartic acid dibenzyl ester tosylate is suitable for chemical biology research aimed at generating amino acid-based probes and labeling handles derived from aspartate side-chain chemistry. The tosylate group provides a reactive site for introducing nucleophile-derived functional groups that can later be adapted into conjugation-ready motifs, while the dibenzyl ester protection helps manage solubility and reactivity during intermediate synthesis. The L-aspartate stereocenter supports consistent spatial presentation of the side-chain substituent, which can be relevant for molecular recognition studies and structure-activity relationship investigations. L-Aspartic acid dibenzyl ester tosylate can therefore be employed to prepare derivatized amino acid scaffolds used in labeling chemistry and biochemical reagent construction.
5. Pharmaceutical Intermediate Preparation
L-Aspartic acid dibenzyl ester tosylate is applied as a chiral intermediate in pharmaceutical intermediate preparation where controlled functional group interconversion is required for route design. The protected ester groups allow handling under conditions that might otherwise cause premature acid-driven side reactions, and the tosylate provides a leaving group suitable for installing substituents that align with medicinal chemistry motifs. The stereodefined L-aspartate core supports downstream conversion into carboxylic acid or amide functionalities commonly encountered in drug-like structures and peptidomimetic candidates. L-Aspartic acid dibenzyl ester tosylate can be integrated into fine chemical synthesis workflows that produce aspartate-derived fragments for medicinal chemistry libraries and process chemistry intermediate generation.
6. Process Chemistry Intermediate
L-Aspartic acid dibenzyl ester tosylate is relevant to process chemistry intermediate development because it combines stable protecting-group behavior with a clear transformation handle on the side chain. The dibenzyl ester protection can be managed to maintain functional-group compatibility across multistep sequences, while the tosylate leaving group enables predictable substitution chemistry to access a range of aspartate-derived derivatives. The defined L-stereochemistry supports reproducible intermediate quality for downstream conversion into activated acids, amides, or peptide coupling partners. L-Aspartic acid dibenzyl ester tosylate therefore serves as a manufacturable chiral amino acid intermediate for specialty chemical production and industrial-scale fine chemical synthesis where functional group orchestration impacts overall route efficiency.
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