(2R,3S)-5-(acetyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate

• ChemBase ID: 91575
• Molecular Formular: C21H20O7
• Molecular Mass: 384.3793
• Monoisotopic Mass: 384.12090298
• SMILES: CC(=O)OC1C[C@H](OC(=O)c2ccccc2)[C@@H](COC(=O)c2ccccc2)O1
• Canonical SMILES: CC(=O)OC1O[C@@H]([C@H](C1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C21H20O7/c1-14(22)26-19-12-17(28-21(24)16-10-6-3-7-11-16)18(27-19)13-25-20(23)15-8-4-2-5-9-15/h2-11,17-19H,12-13H2,1H3/t17-,18+,19?/m0/s1
• InChIKey: OKAAPNNOKHRHLI-PAMZHZACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S)-5-(acetyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3S)-5-(acetyloxy)-2-[(benzoyloxy)methyl]oxolan-3-yl benzoate
• Synonyms: 1-O-Acetyl-2-deoxy-3,5-di-O-benzoylribofuranose; 2-Deoxy-D-erythro-pentofuranose 1-Acetate 3,5-Dibenzoate; 1-Acetyl-2-deoxy-3,5-di-O-benzoylribofuranose

Database IDs

• CAS Number: 51255-12-0
• MDL Number: MFCD00269868
• PubChem SID: 162078274
• PubChem CID: 14731735

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 4.030159
• LogD (pH = 7.4): 4.030159
• Log P: 4.030159
• Molar Refractivity: 97.2457 cm^3
• Polarizability: 38.752792 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 98-100°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A173500

A useful synthetic intermediate for the production of antiviral and anticancer research chemicals.

REFERENCES

• Ohno, M., et al.: Anticancer Agents Based on Natural Product Models, 16, 73 (1980)
• Sonveaux, E., et al.: Bioorg. Chem., 14, 274 (1980)
• De Clercq, E., et al.: Antiviral Res., 12, 1 (1989)