(-)-Dimethyl 2,3-O-isopropylidene-L-tartrate

CAS: 37031-29-1

Ref. TR-D474240

Product Information

• 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 (4R,5R)-2,2,Dimethyl-1,3-dioxolane-4,5-dicarboxylate, Dimethyl L-tartarte Acetonide, (-)-Dimethyl-2,3-O-isopropylidene-<span class="text-smallcaps">L</span>-tartrate, (4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester, 1,3-Dioxolane-4,5-dicarboxylic acid, 2,2-dimethyl-, 4,5-dimethyl ester, (4R,5R)-, 1,3-Dioxolane-4,5-dicarboxylic acid, 2,2-dimethyl-, dimethyl ester, (4R-trans)-, 1,3-dioxolane-4,5-dicarboxylic acid, 2,2-dimethyl-, dimethyl ester, (4R,5R)-, 2,3-Di-O-isopropylidene-<span class="text-smallcaps">L</span>-tartrate, 37031-29-1, 4,5-Dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate, Dimethyl <span class="text-smallcaps">L</span>-tartarte acetonide, dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate, dimethyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

Description

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.
References Chen, 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)

• Brand: TRC

Chemical properties

• Molecular weight: 218.21
• Formula: C₉H₁₄O₆
• Color/Form: Neat
• InChI: InChI=1S/C9H14O6/c1-9(2)14-5(7(10)12-3)6(15-9)8(11)13-4/h5-6H,1-4H3/t5-,6-/m1/s1
• InChI key: InChIKey=ROZOUYVVWUTPNG-PHDIDXHHSA-N
• SMILES: COC(=O)[C@@H]1OC(C)(C)O[C@H]1C(=O)OC