384313

(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate

98%

• Synonym(s): (4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester, Dimethyl (4S,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate
• Empirical Formula (Hill Notation): C₉H₁₄O₆
• CAS Number: 37031-30-4
• Molecular Weight: 218.20
• Beilstein/REAXYS Number: 3548490
• MDL number: MFCD00040504
• UNSPSC Code: 12352005
• PubChem Substance ID: 24863661
• NACRES: NA.22

Properties

• assay: 98%
• form: liquid
• optical activity: [α]20/D +54°, neat
• refractive index: n20/D 1.439 (lit.)
• bp: 80-82 °C/0.1 mmHg (lit.)
• density: 1.19 g/mL at 25 °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-/m0/s1
• InChI key: ROZOUYVVWUTPNG-WDSKDSINSA-N

Description

General description

(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate is a chiral reagent used in organic synthesis. It is prepared by the reaction-rectification process from D -tartrate, and 2,2-dimethoxypropane.{138]

Application

(+)-Dimethyl 2,3-O-isopropylidene-D-tartrate can be used as a starting material for the synthesis of:

• Deuterated 1-deoxy-D-xylose.
• C-terminal peptide -oxo-aldehydes using Fmoc solid-phase peptide synthesis methodology (SPPS).
• Bis-Weinreb amide, a key intermediate for the preparation of myo-inositol analog via ring-closing metathesis.

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: 275.0 °F - closed cup
• flash_point_c: 135 °C - closed cup
• ppe: Eyeshields, Gloves