(2R,3R)-2-[(benzoyloxy)methyl]-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate

• ChemBase ID: 165898
• Molecular Formular: C19H16F2O6
• Molecular Mass: 378.3235464
• Monoisotopic Mass: 378.09149467
• SMILES: [C@@H]1(C(C(O[C@@H]1COC(=O)c1ccccc1)O)(F)F)OC(=O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)OC[C@H]1OC(C([C@@H]1OC(=O)c1ccccc1)(F)F)O
• InChI: InChI=1S/C19H16F2O6/c20-19(21)15(27-17(23)13-9-5-2-6-10-13)14(26-18(19)24)11-25-16(22)12-7-3-1-4-8-12/h1-10,14-15,18,24H,11H2/t14-,15-,18?/m1/s1
• InChIKey: PRZDMMRKPZAYHW-QOYAAKSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2-[(benzoyloxy)methyl]-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3R)-2-[(benzoyloxy)methyl]-4,4-difluoro-5-hydroxyoxolan-3-yl benzoate
• Synonyms: 3,5-Di-O-benzoyl-2,2-difluoro-2-deoxyribose; 2-Deoxy-2,2-difluoro-D-erythro-ribofuranose-3,5-dibenzoate

Database IDs

• CAS Number: 143157-22-6
• PubChem SID: 162260031
• PubChem CID: 11760620

CALCULATED PROPERTIES

• Acid pKa: 9.756082
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.019349
• LogD (pH = 7.4): 4.017466
• Log P: 4.019373
• Molar Refractivity: 88.3104 cm^3
• Polarizability: 34.477165 Å^3
• Polar Surface Area: 82.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: Brown Semi Solid

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D232785

Gemcitabine intermediate.

REFERENCES

• Balzarini, J., et al.: Biochem. Pharmacol., 1988, 37, 2847 (1988)
• Hertel, L., et al.: Cancer Res., 50, 4417 (1988)
• Marquez, V., et al.: J. Med. Chem., 33, 978 (1988)