[(2R,3R,5S)-3-(benzoyloxy)-5-[2,4-dioxo-1,2,3,4-tetrahydro(2-13C,1,3-15N2)pyrimidin-1-yl]-4,4-difluorooxolan-2-yl]methyl benzoate

• ChemBase ID: 168037
• Molecular Formular: C23H18F2N2O7
• Molecular Mass: 475.37449903
• Monoisotopic Mass: 475.10563199
• SMILES: [C@@H]1(C([C@H](O[C@@H]1COC(=O)c1ccccc1)[15n]1[13c](=O)[15nH]c(=O)cc1)(F)F)OC(=O)c1ccccc1
• Canonical SMILES: O=c1cc[15n]([13c](=O)[15nH]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/i22+1,26+1,27+1
• InChIKey: DBSVRWFIIMWGLT-MXOJBCDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,5S)-3-(benzoyloxy)-5-[2,4-dioxo-1,2,3,4-tetrahydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-1-yl]-4,4-difluorooxolan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,3R,5S)-3-(benzoyloxy)-5-[2,4-dioxo(2-^1^3C,1,3-^1^5N₂)-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-13C,15N2; 1'-Epi 3,5-Dibenzoate-2,2-difluorouridine-13C,15N2

Database IDs

• PubChem SID: 162262169
• PubChem CID: 71316351

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: Chloroform; Dichloromethane; Ethanol; Methanol
• Apperance: Amorphous White Solid
• Melting Point: 63-73°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E584502

A labelled intermediate in the synthesis of geminal difluoro nucleoside (α-anomer).

REFERENCES

• Wiley, J., et al.: J. Clin. Invest., 69, 479 (1982)
• Gandhi, V., et al.: Cancer Res., 50, 3675 (1982)
• Abbruzzese, J., et al.: J. Clin. Oncol., 9, 491 (1982)
• Flanagan, S., et al.: J. Biol. Chem., 272, 18026 (1982)