1-[(2S,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 168038
• Molecular Formular: C9H10F2N2O5
• Molecular Mass: 264.1829064
• Monoisotopic Mass: 264.05577787
• SMILES: [C@H]1(C([C@H](O[C@@H]1CO)n1ccc(=O)[nH]c1=O)(F)F)O
• Canonical SMILES: OC[C@H]1O[C@@H](C([C@H]1O)(F)F)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C9H10F2N2O5/c10-9(11)6(16)4(3-14)18-7(9)13-2-1-5(15)12-8(13)17/h1-2,4,6-7,14,16H,3H2,(H,12,15,17)/t4-,6+,7+/m1/s1
• InChIKey: FIRDBEQIJQERSE-PIYBLCFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2S,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2S,4S,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 1-(2-Deoxy-2,2-difluoro-α-D-erythro-pentofuranosyl)-2,4(1H,3H)-pyrimidinedione; 1'-Epi-2'-deoxy-2',2'-difluorouridine; 1'-Epi 2',2'-Difluoro-2'-deoxyuridine

Database IDs

• CAS Number: 153381-14-7
• PubChem SID: 162262170
• PubChem CID: 71316352

CALCULATED PROPERTIES

• Acid pKa: 9.194057
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -1.0843513
• LogD (pH = 7.4): -1.0911082
• Log P: -1.0842645
• Molar Refractivity: 51.2711 cm^3
• Polarizability: 20.00766 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 148-150°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E584800

The epimer of the degradation product of Gemcitabine (G305000), a new antitumor agent.

REFERENCES

• Anliker, S.L., et al.: J. Pharmaceut. Sci., 83, 716 (1994)