(2S,3S)-1,4-dimethoxybutane-2,3-diol

• ChemBase ID: 152687
• Molecular Formular: C6H14O4
• Molecular Mass: 150.17296
• Monoisotopic Mass: 150.08920893
• SMILES: COC[C@@H]([C@H](COC)O)O
• Canonical SMILES: COC[C@@H]([C@H](COC)O)O
• InChI: InChI=1S/C6H14O4/c1-9-3-5(7)6(8)4-10-2/h5-8H,3-4H2,1-2H3/t5-,6-/m0/s1
• InChIKey: QPXJVYUZWDGUBO-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S)-1,4-dimethoxybutane-2,3-diol
• IUPAC Traditional name: (2S,3S)-1,4-dimethoxybutane-2,3-diol
• Synonyms: (-)-1,4-Di-O-methyl-L-threitol; (S,S)-(-)-1,4-Dimethoxy-2,3-butanediol; (-)-1,4-二-邻甲基-L-苏糖醇; (S,S)-(-)-1,4-二甲氧基-2,3-丁二醇

Database IDs

• CAS Number: 50622-10-1
• MDL Number: MFCD00077736
• Beilstein Number: 2322227
• PubChem SID: 162246830; 24864120
• PubChem CID: 10931601

CALCULATED PROPERTIES

• Acid pKa: 13.060271
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.1830959
• LogD (pH = 7.4): -1.1830969
• Log P: -1.1830959
• Molar Refractivity: 35.981 cm^3
• Polarizability: 14.49842 Å^3
• Polar Surface Area: 58.92 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 28-30 °C
• Optical Rotation: [α]20/D -1.8±0.1°, c = 1.9% in methanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (sum of enantiomers, GC)
• Empirical Formula (Hill Notation): C6H14O4

DETAILS

Sigma Aldrich - 38715

Other Notes
Chiral auxiliary, modification of LAH1; Condensation of ester enolates and chiral imines to β-lactams2; Auxiliary, reactions of its acetal, review3; Determination of the enantiomeric purity of ketones by acetal formation and 13C-NMR.4
Packaging
1 g in glass bottle