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Description
Ethyl (R)-4-Phenyl-2-(trifluoromethanesulfonyloxy)butyrate from TCI, supplied under catalogue code E0879, is a chiral building block designed for asymmetric synthesis. The compound carries a stereogenic centre of R configuration at the alpha carbon, which is esterified with a trifluoromethanesulfonyl group — one of the strongest leaving groups known in organic chemistry. The combination of a 4-phenylbutyrate chain and an ethyl ester makes it a well-recognised intermediate in synthetic routes toward active compounds containing the homophenylalanine motif. In the laboratory, this reagent is used to install a chiral fragment onto amines or other nucleophiles in a single clean, stereochemically controlled substitution step.
The property that makes this reagent a preferred choice is the reactivity of the triflate group, which allows nucleophilic substitution to proceed at low to moderate temperatures with predictable inversion of configuration. This matters a great deal when the enantiomeric purity of the final product is an absolute requirement, because alternative routes proceeding through a halide or a tosylate often demand harsher conditions that carry a risk of racemisation. The ethyl ester group at the end of the molecule remains available for straightforward hydrolysis or amidation, so the fragment can be carried forward through subsequent steps without additional protecting-group manipulation.
In Indonesian laboratories, this building block is typically encountered in asymmetric synthesis groups at universities and research institutes, and in pharmaceutical development work where a defined stereocentre must be introduced early in a route. It suits method-development studies on stereospecific substitution, the preparation of homophenylalanine-containing targets, and teaching or research programmes where a reliable single-enantiomer starting material is needed rather than a racemate requiring later resolution.
Laboratory Applications
- Stereospecific nucleophilic substitution with amines — the triflate leaving group departs cleanly under mild conditions, giving predictable inversion at the alpha carbon and preserving the R-derived stereochemical outcome in the product.
- Synthesis of homophenylalanine-containing target molecules — the 4-phenylbutyrate backbone already provides the required carbon framework, so the motif is assembled in fewer steps than de novo construction would require.
- Introduction of chiral fragments onto nucleophiles other than amines — the high reactivity of the triflate ester allows coupling to a range of nucleophilic partners in a single controlled substitution step.
- Asymmetric synthesis route development and optimisation — because substitution runs at low to moderate temperature, chemists can screen conditions without exposing the stereocentre to the racemisation risk associated with harsher halide or tosylate chemistry.
- Downstream ester transformation sequences — the terminal ethyl ester can be hydrolysed or converted to an amide after the chiral fragment is installed, letting the same intermediate serve several branching synthetic pathways.
Specifications
- Brand: TCI (Tokyo Chemical Industry), catalogue code E0879
- CAS number: 88767-98-0
- Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
- Chemical name: Ethyl (R)-4-Phenyl-2-(trifluoromethanesulfonyloxy)butyrate
- Pack sizes: available in standard TCI research and laboratory pack sizes; please confirm the current packaging option when ordering
- Storage: store as directed on the manufacturer label for reactive sulfonate esters
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from moisture, heat sources, and incompatible materials, following the conditions stated on the manufacturer label and safety data sheet. Because the trifluoromethanesulfonate ester is a highly reactive leaving group, contact with water, alcohols, amines, and other nucleophiles should be avoided during storage and weighing. Keep the material in its original tightly sealed container, or transfer it to a clean, dry, chemically compatible vessel with a secure closure. Handle in a fume hood using nitrile gloves, safety glasses, and a laboratory coat, and weigh under dry conditions to prevent hydrolysis and loss of reagent activity. Segregate from strong bases and oxidising agents, label all secondary containers clearly, and dispose of residues and contaminated consumables through the laboratory's chemical waste stream.
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