[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,6-dichloro-9H-purin-9-yl)oxolan-2-yl]methyl acetate

• ChemBase ID: 167151
• Molecular Formular: C16H16Cl2N4O7
• Molecular Mass: 447.22684
• Monoisotopic Mass: 446.03960423
• SMILES: n1c(nc2c(c1Cl)ncn2[C@H]1[C@@H]([C@@H]([C@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)Cl
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc2c1nc(Cl)nc2Cl)COC(=O)C
• InChI: InChI=1S/C16H16Cl2N4O7/c1-6(23)26-4-9-11(27-7(2)24)12(28-8(3)25)15(29-9)22-5-19-10-13(17)20-16(18)21-14(10)22/h5,9,11-12,15H,4H2,1-3H3/t9-,11-,12-,15-/m1/s1
• InChIKey: PYXZXWLFAMZVPY-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,6-dichloro-9H-purin-9-yl)oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-(2,6-dichloropurin-9-yl)oxolan-2-yl]methyl acetate
• Synonyms: NSC 76763; 2,6-Dichloro-9-(2',3',5'-tri-O-acetyl-β-D-ribofuranosyl)purine

Database IDs

• CAS Number: 3056-18-6
• PubChem SID: 162261284
• PubChem CID: 10253027

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.1996526
• LogD (pH = 7.4): 1.199653
• Log P: 1.199653
• Molar Refractivity: 97.0009 cm^3
• Polarizability: 39.08851 Å^3
• Polar Surface Area: 131.73 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; DMSO
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 158-159°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D435850

Protected nucleoside.

REFERENCES

• Elzein, E., et al.: Bioorg. Med. Chem. Lett., 17, 161 (2007)
• Franchetti, P., et al.: J. Med. Chem., 52, 2393 (2007)