1,4-di-tert-butyl (2R,3R)-2,3-dihydroxybutanedioate

• ChemBase ID: 151134
• Molecular Formular: C12H22O6
• Molecular Mass: 262.29948
• Monoisotopic Mass: 262.14163842
• SMILES: CC(C)(C)OC(=O)[C@@H]([C@H](C(=O)OC(C)(C)C)O)O
• Canonical SMILES: O[C@H]([C@H](C(=O)OC(C)(C)C)O)C(=O)OC(C)(C)C
• InChI: InChI=1S/C12H22O6/c1-11(2,3)17-9(15)7(13)8(14)10(16)18-12(4,5)6/h7-8,13-14H,1-6H3/t7-,8-/m1/s1
• InChIKey: ITWOKJQQGHCDBL-HTQZYQBOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-di-tert-butyl (2R,3R)-2,3-dihydroxybutanedioate
• IUPAC Traditional name: 1,4-di-tert-butyl (2R,3R)-2,3-dihydroxybutanedioate
• Synonyms: (+)-Di-tert-butyl L-tartrate; (+)-二叔丁基 L-酒石酸

Database IDs

• CAS Number: 117384-45-9
• MDL Number: MFCD00192000
• Beilstein Number: 5026723
• PubChem SID: 24890140; 24890142; 162245292; 24866303
• PubChem CID: 9943166

CALCULATED PROPERTIES

• Acid pKa: 11.184804
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.57090664
• LogD (pH = 7.4): 0.5708363
• Log P: 0.57090753
• Molar Refractivity: 63.3628 cm^3
• Polarizability: 25.718498 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 90-92 °C; 90-92 °C(lit.)
• Optical Rotation: [α]20/D +11±1°, c = 1% in acetone; [α]20/D +11°, c = 1 in acetone

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% (sum of enantiomers, GC); 99%
• Grade: purum; Selectophore™
• Optical Purity: enantiomeric ratio: ≥99.5:0.5 (GC)
• Linear Formula: [CH(OH)CO2C(CH3)3]2

DETAILS

Sigma Aldrich - 420026

Packaging
50 mg in glass bottle

Sigma Aldrich - 95357

Legal Information
Selectophore is a trademark of Sigma-Aldrich GmbH

Sigma Aldrich - 95359

Other Notes
Bulky tartaric ester useful as auxiliary; e.g. asymmetric opening of epoxides with trimethylsilyl azide1; Increasing steric bulk of tartaric esters often leads to higher stereoselectivity in reactions2,3