D474240 Chemical Structure

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Product Description

Catalogue NumberD474240
Chemical Name(-)-Dimethyl 2,3-O-isopropylidene-L-tartrate
Synonyms(4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic Acid 4,5-Dimethyl Ester; (4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic Acid Dimethyl Ester; (4R-trans)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic Acid Dimethyl Ester; (-)-Dimethyl-2,3-O-isopropylidene-L-tartrate; Dimethyl (4R,5R)-2,2,Dimethyl-1,3-dioxolane-4,5-dicarboxylate; Dimethyl L-tartarte Acetonide
CAS Number37031-29-1
Molecular FormulaC₉H₁₄O₆
AppearanceColourless Oil
Molecular Weight218.21
StorageRefrigerator, Under inert atmosphere
SolubilityChloroform (Slightly), Methanol (Slightly)
Category Building Blocks; Chiral Molecules;
Applications(-)-Dimethyl 2,3-O-isopropylidene-L-tartrate is used as a reagent to synthesize (+)-Migrastatin, a natural macrolide compound produced by Streptomyces 1 & 2 that acts as a tumour migration cell inhibitor. (-)-Dimethyl 2,3-O-isopropylidene-L-tartrate is also a derivative of Tartaric acid (L-isomer: T007630 & D-isomer: T007625), a compound that is used as a chiral complexing agent in synthetic chemistry.
ReferencesChen, L., et al.: Nature, 464, 1062 (2010); Gaul, C., et al.: J. Am. Chem. Soc., 125, 6042 (2003); Heldin, E., et al.: Chromatographia, 32, 407 (1991)