(2R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-fluorooxolan-2-yl benzoate

• ChemBase ID: 165945
• Molecular Formular: C26H21FO7
• Molecular Mass: 464.4391432
• Monoisotopic Mass: 464.12713123
• SMILES: C1(F)[C@H](O[C@@H]([C@@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: FC1[C@H](O[C@@H]([C@@H]1OC(=O)c1ccccc1)COC(=O)c1ccccc1)OC(=O)c1ccccc1
• InChI: InChI=1S/C26H21FO7/c27-21-22(33-24(29)18-12-6-2-7-13-18)20(16-31-23(28)17-10-4-1-5-11-17)32-26(21)34-25(30)19-14-8-3-9-15-19/h1-15,20-22,26H,16H2/t20-,21?,22+,26-/m1/s1
• InChIKey: JOAHVPNLVYCSAN-PPTKZWKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-fluorooxolan-2-yl benzoate
• IUPAC Traditional name: (2R,4S,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-3-fluorooxolan-2-yl benzoate
• Synonyms: 2-Deoxy-2-fluoro-α-D-arabinofuranose 1,3,5-Tribenzoate; 2'-Fluoro-2'-deoxy-1,3,5-tri-O-benzoyl-α-D-arabinofuranose; 2-Deoxy-2-fluoro-1,3,5-tri-O-benzoyl-α-D-arabinofuranose

Database IDs

• CAS Number: 97614-43-2
• PubChem SID: 162260078
• PubChem CID: 71315471

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 6.074787
• LogD (pH = 7.4): 6.074787
• Log P: 6.074787
• Molar Refractivity: 117.7348 cm^3
• Polarizability: 46.177628 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 74-77°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - D235500

Clofarabine intermediate.

REFERENCES

• Williams, A., et al.: Biochem., 48, 11994 (2009)
• Pathak, A., et al.: Bioorg. Med. Chem., 17, 872 (2009)