1,4-bis(propan-2-yl) (2R,3R)-2,3-dihydroxybutanedioate

• ChemBase ID: 74449
• Molecular Formular: C10H18O6
• Molecular Mass: 234.24632
• Monoisotopic Mass: 234.1103383
• SMILES: C(C)(C)OC(=O)[C@H](O)[C@@H](O)C(=O)OC(C)C
• Canonical SMILES: O[C@H]([C@H](C(=O)OC(C)C)O)C(=O)OC(C)C
• InChI: InChI=1S/C10H18O6/c1-5(2)15-9(13)7(11)8(12)10(14)16-6(3)4/h5-8,11-12H,1-4H3/t7-,8-/m1/s1
• InChIKey: XEBCWEDRGPSHQH-HTQZYQBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-bis(propan-2-yl) (2R,3R)-2,3-dihydroxybutanedioate
• IUPAC Traditional name: 1,4-diisopropyl (2R,3R)-2,3-dihydroxybutanedioate
• Synonyms: (2R,3R)-Diisopropyl 2,3-dihydroxysuccinate; L-(+)-Tartaric acid diisopropyl ester; L-(+)-Tartaric acid diisopropyl ester; (+)-Diisopropyl L-tartrate; (+)-二异丙酯-L-(+)-酒石酸; L-(+)-酒石酸二异丙酯

Database IDs

• CAS Number: 2217-15-4
• EC Number: 218-709-0
• MDL Number: MFCD00064450
• Beilstein Number: 1727863
• PubChem SID: 162039368; 24853734
• PubChem CID: 6453580

CALCULATED PROPERTIES

• Acid pKa: 11.185941
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.009753288
• LogD (pH = 7.4): 0.009683163
• Log P: 0.009754182
• Molar Refractivity: 54.0864 cm^3
• Polarizability: 22.078806 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 152 °C/12 mmHg(lit.)
• Flash Point: >110 °C; >230 °F
• Density: 1.114 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.439; n20/D 1.439(lit.)
• Optical Rotation: [α]20/D +16±1°, neat; [α]24/D +17°, neat

Safety Information

• RTECS: WW8100000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (sum of enantiomers, GC); 95+%; 98%
• Grade: purum
• Optical Purity: ee: 99% (GLC)
• Linear Formula: [-CH(OH)CO2CH(CH3)2]2

DETAILS

MP Biomedicals - 02156743

([+]-Diisopropyl L-tartrate)
1 m = approx. 1.11 g

Sigma Aldrich - 229180

Packaging
25, 100 g in glass bottle
Application
Both D- and L-forms are reagents for kinetic resolution of racemic allylic alcohols1,2,3 and α-furfuryl amides4 by enantioselective epoxidation.

Sigma Aldrich - 95364

Other Notes
Chiral catalyst used for the enantioselective epoxidation of allylic alcohols, Sharpless AE1; Auxiliary in chiral allylic boronates2,3; Catalytic trimethylsilyl-cyanation of aldehydes4