(2R,3R)-2,3-dihydroxy-N,N,N',N'-tetramethylbutanediamide

• ChemBase ID: 145996
• Molecular Formular: C8H16N2O4
• Molecular Mass: 204.22364
• Monoisotopic Mass: 204.111007
• SMILES: CN(C)C(=O)[C@@H]([C@H](C(=O)N(C)C)O)O
• Canonical SMILES: O[C@H]([C@H](C(=O)N(C)C)O)C(=O)N(C)C
• InChI: InChI=1S/C8H16N2O4/c1-9(2)7(13)5(11)6(12)8(14)10(3)4/h5-6,11-12H,1-4H3/t5-,6-/m1/s1
• InChIKey: PCYDYHRBODKVEL-PHDIDXHHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxy-N,N,N',N'-tetramethylbutanediamide
• IUPAC Traditional name: (2R,3R)-2,3-dihydroxy-N,N,N',N'-tetramethylbutanediamide
• Synonyms: (+)-L-Tartaric acid bis(dimethylamide); (R,R)-(+)-2,3-Dihydroxy-N,N,N′,N′-tetramethylsuccinamide; (+)-N,N,N′,N′-Tetramethyl-L-tartaric acid diamide; N,N,N',N'-Tetramethyl-L-tartramide; (+)-L-酒石酸双(二甲酰胺); (R,R)-(+)-2,3-二羟基-N,N,N′,N′-四甲基琥珀酰胺; (+)-N,N,N′,N′-四甲基-L-酒石酸二酰胺

Database IDs

• CAS Number: 26549-65-5
• MDL Number: MFCD00025672
• Beilstein Number: 1959244
• PubChem SID: 162240196; 24863441
• PubChem CID: 6610750

CALCULATED PROPERTIES

• Acid pKa: 11.674234
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.5479813
• LogD (pH = 7.4): -2.548004
• Log P: -2.5479808
• Molar Refractivity: 49.4446 cm^3
• Polarizability: 19.263136 Å^3
• Polar Surface Area: 81.08 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 184-186 °C; 184-186 °C(lit.)
• Optical Rotation: [α]20/D +46±2°, c = 3% in ethanol; [α]20/D +46°, c = 3 in ethanol

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, HPLC); 95+%; 98%
• Grade: purum
• Linear Formula: [-CH(OH)CON(CH3)2]2

DETAILS

Sigma Aldrich - 376418

Packaging
25 g in poly bottle
5 g in glass bottle

Sigma Aldrich - 87953

Other Notes
Chiral auxiliary; the corresponding acetals of α,β-unsaturated aldehydes and ketones undergo highly regio- and stereoselective reactions at the double bond. Reactions with organoaluminum reagents1; stereoselective bromolactonization2,3; Preparation of a chiral dioxaborolane ligand for cyclopropanation4