(2R,3R)-3-(benzyloxy)butane-1,2,4-triol

• ChemBase ID: 156300
• Molecular Formular: C11H16O4
• Molecular Mass: 212.24234
• Monoisotopic Mass: 212.10485899
• SMILES: c1ccc(cc1)CO[C@H](CO)[C@@H](CO)O
• Canonical SMILES: OC[C@H]([C@@H](CO)O)OCc1ccccc1
• InChI: InChI=1S/C11H16O4/c12-6-10(14)11(7-13)15-8-9-4-2-1-3-5-9/h1-5,10-14H,6-8H2/t10-,11-/m1/s1
• InChIKey: YYGZBCNOJHZTGA-GHMZBOCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-3-(benzyloxy)butane-1,2,4-triol
• IUPAC Traditional name: (2R,3R)-3-(benzyloxy)butane-1,2,4-triol
• Synonyms: (-)-2-O-Benzyl-D-threitol; (2R,3R)-(-)-2-Benzyloxy-1,3,4-butanetriol; (-)-2-O-苄基-D-苏糖醇; (2R,3R)-(-)-2-苄氧基-1,3,4-丁三醇

Database IDs

• CAS Number: 84379-52-2
• MDL Number: MFCD00042969
• Beilstein Number: 4679935
• PubChem SID: 162250438; 24848269
• PubChem CID: 10867592

CALCULATED PROPERTIES

• Acid pKa: 13.312514
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.10174935
• LogD (pH = 7.4): -0.101749875
• Log P: -0.101749346
• Molar Refractivity: 55.8424 cm^3
• Polarizability: 22.102644 Å^3
• Polar Surface Area: 69.92 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 75-77 °C
• Optical Rotation: [α]20/D -16.5±1°, c = 1% in ethanol

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

• Empirical Formula (Hill Notation): C11H16O4

DETAILS

Sigma Aldrich - 13624

Other Notes
Chiral building block, used in the synthesis of glycerides;1,2 3,4-O-isopropylidenation and 1-oxidation to the aldehyde;3 oxidative cleavage to the 2-O-benzylglyceraldehyde, which is stable but undergoes oligomerization.4,5
Packaging
1 g in glass bottle