Product Description
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester, commonly known as Diethyl L-tartrate, is a chiral chemical compound used extensively in synthetic organic chemistry. As the L-(-) enantiomer of diethyl tartrate, it serves as a crucial chiral auxiliary and building block. Its primary value lies in asymmetric synthesis, particularly in the Sharpless epoxidation process, where it enables the predictable and highly selective conversion of allylic alcohols into epoxides. This makes it an indispensable tool in the production of complex, enantiomerically pure molecules for the pharmaceutical and fine chemical industries.
Product Properties
Property Value CAS Number 13811-71-7 Common Name Diethyl L-tartrate Chemical Formula C₈H₁₄O₆ Molar Mass 206.19 g/mol Appearance Colorless to pale yellow liquid Boiling Point 280 °C (536 °F; 553 K) Density 1.2 g/mL Synonyms L-(-)-Diethyl tartrate, Diethyl (2S,3S)-tartrate, L-DET Product Usage
(2S,3S)(-)-Dihydroxybutane-1,4-dioic acid diethyl ester is a versatile reagent with several important applications:
- Asymmetric Epoxidation: It is a key chiral ligand in the Sharpless asymmetric epoxidation, used to synthesize optically active epoxides from primary and secondary allylic alcohols.
- Chiral Synthesis: Serves as a versatile chiral building block for the synthesis of various pharmaceutical active ingredients (APIs) and natural products.
- Precursor for Chiral Ligands: Used as a starting material to create other complex chiral ligands and auxiliaries for asymmetric catalysis.
- Food Additive & Fragrance: Utilized in some cases as a food additive and as a component in fragrance compositions due to its ester functionality.
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