(2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-[(benzoyloxy)methyl]-4,4-difluorooxolan-3-yl benzoate

• ChemBase ID: 168054
• Molecular Formular: C23H19F2N3O6
• Molecular Mass: 471.4102664
• Monoisotopic Mass: 471.12419178
• SMILES: n1c(=O)n(ccc1N)[C@H]1C([C@@H]([C@@H](COC(=O)c2ccccc2)O1)OC(=O)c1ccccc1)(F)F
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H](C1(F)F)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C23H19F2N3O6/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)28-12-11-17(26)27-22(28)31/h1-12,16,18,21H,13H2,(H2,26,27,31)/t16-,18+,21-/m1/s1
• InChIKey: ZPUUYUUQQGBHBU-PLMTUMEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-[(benzoyloxy)methyl]-4,4-difluorooxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-2-[(benzoyloxy)methyl]-4,4-difluorooxolan-3-yl benzoate
• Synonyms: 4-Amino-1-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-D-threo-pentofuranosyl)-2(1H)-pyrimidinone; 3'-Epi Gemcitabine 3',5'-Dibenzoate

Database IDs

• CAS Number: 1268237-46-2
• PubChem SID: 162262186
• PubChem CID: 29976925

CALCULATED PROPERTIES

• Acid pKa: 17.94884
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 3.52406
• LogD (pH = 7.4): 3.52406
• Log P: 3.52406
• Molar Refractivity: 112.8943 cm^3
• Polarizability: 43.351196 Å^3
• Polar Surface Area: 120.52 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Off-White Solid
• Melting Point: 92-94°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E588516

Intermediate in the preparation of Gemcitabine (G305000) impurities.