[(2R,3S,4R,5R,6S)-4-(benzoyloxy)-6-(benzyloxy)-5-acetamido-3-hydroxyoxan-2-yl]methyl benzoate

• ChemBase ID: 161372
• Molecular Formular: C29H29NO8
• Molecular Mass: 519.54246
• Monoisotopic Mass: 519.18931689
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)c1ccccc1)OCc1ccccc1)NC(=O)C)OC(=O)c1ccccc1)O
• Canonical SMILES: CC(=O)N[C@@H]1[C@@H](OCc2ccccc2)O[C@H]([C@H]([C@@H]1OC(=O)c1ccccc1)O)COC(=O)c1ccccc1
• InChI: InChI=1S/C29H29NO8/c1-19(31)30-24-26(38-28(34)22-15-9-4-10-16-22)25(32)23(18-35-27(33)21-13-7-3-8-14-21)37-29(24)36-17-20-11-5-2-6-12-20/h2-16,23-26,29,32H,17-18H2,1H3,(H,30,31)/t23-,24-,25-,26-,29+/m1/s1
• InChIKey: MYVKGGKJMHXHHZ-FSJVOCHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6S)-4-(benzoyloxy)-6-(benzyloxy)-5-acetamido-3-hydroxyoxan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,3S,4R,5R,6S)-4-(benzoyloxy)-6-(benzyloxy)-5-acetamido-3-hydroxyoxan-2-yl]methyl benzoate
• Synonyms: Phenylmethyl 2-(Acetylamino)-2-deoxy-α-D-glucopyranoside 3,6-Dibenzoate; Benzyl 2-Acetamido-3,6-di-O-benzoyl-2-deoxy-α-D-glucopyranoside

Database IDs

• CAS Number: 82827-77-8
• PubChem SID: 162255507
• PubChem CID: 15756204

CALCULATED PROPERTIES

• Acid pKa: 12.095581
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 4.1376247
• LogD (pH = 7.4): 4.137617
• Log P: 4.1376247
• Molar Refractivity: 136.0325 cm^3
• Polarizability: 53.764206 Å^3
• Polar Surface Area: 120.39 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 159-160°C

REFERENCES

• Gallo-Rodriguez, C. et al.: J. Org. Chem. 61, 1886-1889 (1996)