CAS 87-91-2 Diethyl L-(+)-Tartrate - Catalysts / Alfa Chemistry

Synonyms

FEMA No. 2378; l-tartaric acid diethyl ester; FT-0624841; Tartaric acid, diethyl ester, (R,R)-; Diethyl L-tartrate, >=99%, FG; L-Tartaric acid diethyl; NSC 44808; RTR-027622; DTXSID5052597; diethyl (2R,3R)-2,3-bis(oxidanyl)butanedioate;

IUPAC Name

diethyl (2R,3R)-2,3-dihydroxybutanedioate;

Molecular Weight

206.194g/mol

Molecular Formula

C8H14O6;

Canonical SMILES

CCOC(=O)C(C(C(=O)OCC)O)O;

InChI

InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m1/s1;

InChI Key

YSAVZVORKRDODB-PHDIDXHHSA-N;

Melting Point

17.0°C;

Storage

Store below +30°C.

Complexity

180

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

201-783-3

Exact Mass

206.079g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

206.079g/mol

Rotatable Bond Count

Topological Polar Surface Area

93.1A^2

UNII

OQ72CPY58Z

Application

Diethyl L-(+)-Tartrate serves as a versatile chiral reagent and auxiliary in numerous chemical transformations, thanks to its origins in natural tartaric acid. It plays a crucial role in the Sharpless enantioselective epoxidation of allylic alcohols and the oxidation of sulfides to sulfoxides, as well as assisting in the enantioselective construction of cyclopropanes through an asymmetric Simmons-Smith reaction. Notably, this compound is instrumental in synthesizing isoquinoline alkaloids and arundic acid, with applications extending to acute ischemic stroke therapy. Furthermore, it contributes to the creation of biologically active compounds such as (+)-altholactone, (-)-aspicilin, (+)-monomorine I, and (+)-(1R,2R,3S,6S)-3,6-di-O-methyl conduritol-E, all while imparting a mild, fruity, wine-like aroma.

February 11, 2025

Exceptional Chiral Reagent for Research Applications

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