CAS 608-68-4 Dimethyl L-(+)-Tartrate - Catalysts / Alfa Chemistry

Synonyms

ST24026154; Dimethyl (R(R*,R*))-tartrate; Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, dimethyl ester; L-(+)-Tartaric acid, dimethyl ester; L(+)tartaric acid dimethyl ester; TR-020984; (+)-DimethylL-tartrate; STR02392; l-Tartaric acid, dimethyl ester; Dimethyl L-tartrate;

IUPAC Name

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

Molecular Weight

178.14g/mol

Molecular Formula

C6H10O6;

Canonical SMILES

COC(=O)C(C(C(=O)OC)O)O;

InChI

InChI=1S/C6H10O6/c1-11-5(9)3(7)4(8)6(10)12-2/h3-4,7-8H,1-2H3/t3-,4-/m1/s1;

InChI Key

PVRATXCXJDHJJN-QWWZWVQMSA-N;

Complexity

157

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

EC Number

210-166-8

Exact Mass

178.048g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

178.048g/mol

Rotatable Bond Count

Topological Polar Surface Area

93.1A^2

Application

Dimethyl L-(+)-Tartrate serves as a versatile starting reagent widely utilized in various chemical syntheses. Primarily, it plays a crucial role in the synthesis of (+)-Monomorine I, an important pyrrolidine-based alkaloid that functions as a trail pheromone for the Pharaoh's ant, Monomorium pharaonis. Additionally, it can be transformed through a reaction with sulfur tetrafluoride to yield dimethyl meso-2,3-difluorosuccinate. Furthermore, Dimethyl L-(+)-Tartrate is instrumental in synthesizing several chiral ligands used in asymmetric synthesis, including (2R, 3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol, (-)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane (PYDIPHOS), and (4R,5R)-α,α,α',α'-2,2-hexaphenyl-4,5-dimethanol-1,3-dioxolane. With its range of applications, this colorless to light yellow liquid is an essential component in advancing chemical research and development.

April 14, 2025

Versatile Reagent for Chiral Synthesis

Dimethyl L-(+)-Tartrate was perfect for our research on synthesizing chiral ligands. Its reactivity, especially with sulfur tetrafluoride, streamlined our process in developing novel compounds. Highly recommend for efficient asymmetric synthesis work.