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

• ChemBase ID: 161554
• 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-DRYUAMBJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Phenylmethyl D-Glucopyranoside; Benzyl D-Glucopyranoside (An alpha-beta mixture); Phenylmethyl α-D-Mannopyranoside; Benzyl α-D-Mannopyranoside

Database IDs

• CAS Number: 15548-45-5; 34246-23-6
• PubChem SID: 162255689
• PubChem CID: 46783435

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: Methanol; warm Ethanol; Water; Water
• Apperance: White Solid
• Melting Point: 126-129°C

Safety Information

• Storage Condition: -20°C Freezer; Hygroscopic, -20°C Freezer, Under Inert Atmosphere

REFERENCES

• Rutschow, S., et al.: Bioorg., Med. Chem., 10, 4043 (2002)
• Duvet, S., et al.: Glycobiol., 14, 841 (2002)