359068

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

97%

• Synonym(s): (4R,5R)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester, Dimethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
• Empirical Formula (Hill Notation): C₉H₁₄O₆
• CAS Number: 37031-29-1
• Molecular Weight: 218.20
• Beilstein/REAXYS Number: 15406
• MDL number: MFCD00066218
• UNSPSC Code: 12352005
• PubChem Substance ID: 24862049
• NACRES: NA.22

Properties

• assay: 97%
• form: liquid
• optical activity: [α]20/D −54°, neat
• refractive index: n20/D 1.439 (lit.)
• bp: 150 °C/19 mmHg (lit.)
• density: 1.190 g/mL at 20 °C (lit.)
• SMILES string: COC(=O)[C@@H]1OC(C)(C)O[C@H]1C(=O)OC
• 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: ROZOUYVVWUTPNG-PHDIDXHHSA-N

Description

Application

(-)-Dimethyl 2,3-O-isopropylidene-L-tartrate may be used as a starting material in the total synthesis of (+)-migrastatin and also in the synthesis of a structural analog of S-ribosylhomocysteinase (LuxS), which acts as a potent competitive inhibitor against LuxS.

Valuable building block for TADDOL chiral auxiliaries, dipyridine ligands, and threitols.

Safety Information

• Storage Class: 10 - Combustible liquids
• wgk_germany: WGK 3
• flash_point_f: 230.0 °F - closed cup
• flash_point_c: 110 °C - closed cup
• ppe: Eyeshields, Gloves