[(2R,3S,5S)-3-(benzoyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4,4-difluorooxolan-2-yl]methyl benzoate

• ChemBase ID: 168039
• Molecular Formular: C23H18F2N2O7
• Molecular Mass: 472.3950264
• Monoisotopic Mass: 472.10820737
• SMILES: [C@H]1(C([C@H](O[C@@H]1COC(=O)c1ccccc1)n1ccc(=O)[nH]c1=O)(F)F)OC(=O)c1ccccc1
• Canonical SMILES: O=c1ccn(c(=O)[nH]1)[C@H]1O[C@@H]([C@@H](C1(F)F)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C23H18F2N2O7/c24-23(25)18(34-20(30)15-9-5-2-6-10-15)16(13-32-19(29)14-7-3-1-4-8-14)33-21(23)27-12-11-17(28)26-22(27)31/h1-12,16,18,21H,13H2,(H,26,28,31)/t16-,18+,21+/m1/s1
• InChIKey: DBSVRWFIIMWGLT-MMOPVJDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,5S)-3-(benzoyloxy)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4,4-difluorooxolan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,3S,5S)-3-(benzoyloxy)-5-(2,4-dioxo-3H-pyrimidin-1-yl)-4,4-difluorooxolan-2-yl]methyl benzoate
• Synonyms: 1-(3,5-Di-O-benzoyl-2-deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione; 1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate

Database IDs

• CAS Number: 143157-24-8
• PubChem SID: 162262171
• PubChem CID: 29979335

CALCULATED PROPERTIES

• Acid pKa: 9.196126
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.9062488
• LogD (pH = 7.4): 3.8995245
• Log P: 3.906335
• Molar Refractivity: 110.9151 cm^3
• Polarizability: 42.74635 Å^3
• Polar Surface Area: 111.24 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - E584805

Protected epimer of a Gemcitabine degradation product.