2-[(2R,4R,5S)-2,4-bis(benzyloxy)-6-[(benzyloxy)methyl]-5-hydroxyoxan-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 161488
• Molecular Formular: C35H33NO7
• Molecular Mass: 579.63902
• Monoisotopic Mass: 579.2257024
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1COCc1ccccc1)OCc1ccccc1)N1C(=O)c2c(C1=O)cccc2)OCc1ccccc1)O
• Canonical SMILES: O[C@@H]1C(COCc2ccccc2)O[C@H](C([C@H]1OCc1ccccc1)N1C(=O)c2c(C1=O)cccc2)OCc1ccccc1
• InChI: InChI=1S/C35H33NO7/c37-31-29(23-40-20-24-12-4-1-5-13-24)43-35(42-22-26-16-8-3-9-17-26)30(32(31)41-21-25-14-6-2-7-15-25)36-33(38)27-18-10-11-19-28(27)34(36)39/h1-19,29-32,35,37H,20-23H2/t29?,30?,31-,32-,35-/m1/s1
• InChIKey: RXHWITVEJRNKIS-URFFWBCKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2R,4R,5S)-2,4-bis(benzyloxy)-6-[(benzyloxy)methyl]-5-hydroxyoxan-3-yl]-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-[(2R,4R,5S)-2,4-bis(benzyloxy)-6-[(benzyloxy)methyl]-5-hydroxyoxan-3-yl]isoindole-1,3-dione
• Synonyms: Phenylmethyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,6-bis-O-(phenylmethyl)-β-D-glucopyranoside; Benzyl 2-Deoxy-2-phthalimido-3,6-di-O-benzyl-β-D-glucopyranoside

Database IDs

• CAS Number: 80035-36-5
• PubChem SID: 162255623
• PubChem CID: 46783556

CALCULATED PROPERTIES

• Acid pKa: 13.078056
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 5.6059356
• LogD (pH = 7.4): 5.605935
• Log P: 5.605936
• Molar Refractivity: 159.965 cm^3
• Polarizability: 62.135403 Å^3
• Polar Surface Area: 94.53 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Colourless Oil

REFERENCES

• Hagihara, S., et al.: J. Med. Chem., 48, 3126 (2005)
• Nakano, J., et al.: Bioorg. Med. Chem. Lett., 16, 928 (2005)