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Description
TCI D2686 (-)-Dipivaloyl-L-tartaric Acid is a chiral building block derived from L-tartaric acid, in which both hydroxyl groups have been acylated with bulky pivaloyl groups. In asymmetric chemistry laboratories, tartaric acid derivatives play an important role as enantiomer resolving reagents, chiral ligands, and sources of stereochemical information for directed synthesis. The two carboxylic acid groups that remain free allow this compound to form salts with racemic bases, while the chiral framework at the centre of the molecule governs the crystal packing pattern that distinguishes one enantiomer of the pair from the other.
The characteristic that makes this compound an attractive choice is the pivaloyl group, which is highly demanding in steric terms and therefore provides a more sharply defined chiral environment than simpler tartrate derivatives. This large steric bulk frequently amplifies the solubility difference between the diastereomeric salts that form, a key factor in the success of a resolution carried out by crystallisation. The compound also originates from a naturally occurring chiral feedstock that is available in both configurations, so researchers can design experiments with clear and deliberate stereochemical control.
In Indonesian laboratories, a reagent of this type is typically used in asymmetric synthesis groups at universities and research institutes, as well as in pharmaceutical and fine chemical development work where a single enantiomer of an active compound must be obtained. Its solid form makes it convenient to weigh out for small-scale trials, and it is normally kept as part of a chiral reagent set alongside other tartaric acid derivatives so that several resolving agents can be screened against one racemic substrate.
Laboratory Applications
Resolution of racemic amines: the two free carboxylic acid groups form diastereomeric salts with basic racemates, and the bulky pivaloyl groups sharpen the solubility difference that drives separation by crystallisation.
Chiral ligand preparation: the defined stereocentres of the tartrate backbone make this compound a starting point for building ligands used in stereoselective transformations in asymmetric chemistry laboratories.
Diastereomeric salt crystallisation screening: researchers evaluate it alongside simpler tartrate derivatives to identify which resolving agent gives the cleanest crystal packing difference for a given substrate.
Asymmetric synthesis method development: because it derives from a natural chiral feedstock available in both configurations, it supports experiments designed with deliberate and verifiable stereochemical control.
Chiral building block incorporation: the tartrate framework transfers stereochemical information into target molecules during directed synthesis of single-enantiomer intermediates.
Specifications
Brand: TCI
CAS number: 65259-81-6
Category: Chemistry > Asymmetric Synthesis > Chiral Building Blocks
Product code: D2686
Physical form: solid
Pack sizes: available in the standard TCI catalogue pack sizes for this product code
Storage: keep in a closed container in a cool, dry place
Handling and Storage
Store the material in its original tightly closed container in a cool, dry and well ventilated area, away from moisture, direct sunlight and sources of heat. Glass or chemically compatible plastic containers with a secure closure are suitable for storing and dispensing weighed portions. As with any carboxylic acid derivative, handle it in a fume hood or a well ventilated workspace and wear a laboratory coat, safety glasses and chemical resistant gloves, avoiding contact with skin and eyes and inhalation of dust. Use a clean, dry spatula each time to prevent contamination of the bulk material, close the container immediately after use, and consult the manufacturer's safety data sheet before handling, including for disposal of residues.
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