(2R,4S,5S)-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 161555
• Molecular Formular: C13H18O6
• Molecular Mass: 270.27842
• Monoisotopic Mass: 270.1103383
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)OCc1ccccc1)O)O)O
• Canonical SMILES: OCC1O[C@@H](OCc2ccccc2)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H18O6/c14-6-9-10(15)11(16)12(17)13(19-9)18-7-8-4-2-1-3-5-8/h1-5,9-17H,6-7H2/t9?,10-,11+,12?,13-/m1/s1
• InChIKey: GKHCBYYBLTXYEV-APSDNXJZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5S)-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,4S,5S)-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Phenylmethyl β-D-Glucopyranoside; Benzyl-O-β-D-glucopyranoside; Benzyl β-D-Glucopyranoside

Database IDs

• CAS Number: 4304-12-5
• PubChem SID: 162255690
• PubChem CID: 71313822

CALCULATED PROPERTIES

• Acid pKa: 12.210496
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.5649397
• LogD (pH = 7.4): -0.5649463
• Log P: -0.5649396
• Molar Refractivity: 65.2872 cm^3
• Polarizability: 26.444118 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 111-112°C

Safety Information

• Storage Condition: -20°C Freezer

REFERENCES

• Yoshikawa, M., et al.: Chem. Pharm. Bull., 56, 1297 (2008)
• Takeda, Y., et al.: J. Nat. Med., 62, 476 (2008)