(2S,3S)-2,3-bis[(2,2-dimethylpropanoyl)oxy]butanedioic acid

• ChemBase ID: 152589
• Molecular Formular: C14H22O8
• Molecular Mass: 318.31968
• Monoisotopic Mass: 318.13146766
• SMILES: CC(C)(C)C(=O)O[C@@H]([C@@H](C(=O)O)OC(=O)C(C)(C)C)C(=O)O
• Canonical SMILES: OC(=O)[C@H]([C@@H](C(=O)O)OC(=O)C(C)(C)C)OC(=O)C(C)(C)C
• InChI: InChI=1S/C14H22O8/c1-13(2,3)11(19)21-7(9(15)16)8(10(17)18)22-12(20)14(4,5)6/h7-8H,1-6H3,(H,15,16)(H,17,18)/t7-,8-/m0/s1
• InChIKey: UFHJEZDFEHUYCR-YUMQZZPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-2,3-bis[(2,2-dimethylpropanoyl)oxy]butanedioic acid
• IUPAC Traditional name: (2S,3S)-2,3-bis[(2,2-dimethylpropanoyl)oxy]butanedioic acid
• Synonyms: (+)-DPTA; (+)-O,O′-Di-pivaloyl-D-tartaric acid; (+)-O,O′-二特戊酰基-D-酒石酸

Database IDs

• CAS Number: 76769-55-6
• MDL Number: MFCD00015634
• Beilstein Number: 6894779
• PubChem SID: 24867201; 162246734
• PubChem CID: 16212279

CALCULATED PROPERTIES

• Acid pKa: 3.3272338
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.09568137
• LogD (pH = 7.4): -2.8415277
• Log P: 2.6525238
• Molar Refractivity: 71.9212 cm^3
• Polarizability: 29.32641 Å^3
• Polar Surface Area: 127.2 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 127-130 °C(lit.)
• Optical Rotation: [α]20/D +23.5±1°, c = 1.7% in dioxane

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0%
• Linear Formula: [(CH3)3CCO2CH(CO2H)-]2

DETAILS

Sigma Aldrich - 43456

Other Notes
Reagent for the "deracemization" of carbonyl compounds by enantio-selective protonation of enamines or Li-enolates 1,2,3; Synthesis of optically active α-amino acids 4
Packaging
5 g in glass bottle