[(2R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-(5-iodo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl benzoate

• ChemBase ID: 166878
• Molecular Formular: C23H18FIN2O7
• Molecular Mass: 580.3010932
• Monoisotopic Mass: 580.01427715
• SMILES: [nH]1c(=O)n(cc(c1=O)I)[C@H]1[C@H](C(OC(=O)c2ccccc2)[C@@H](COC(=O)c2ccccc2)O1)F
• Canonical SMILES: O=C(c1ccccc1)OC[C@H]1O[C@H]([C@H](C1OC(=O)c1ccccc1)F)n1cc(I)c(=O)[nH]c1=O
• InChI: InChI=1S/C23H18FIN2O7/c24-17-18(34-22(30)14-9-5-2-6-10-14)16(12-32-21(29)13-7-3-1-4-8-13)33-20(17)27-11-15(25)19(28)26-23(27)31/h1-11,16-18,20H,12H2,(H,26,28,31)/t16-,17-,18?,20-/m1/s1
• InChIKey: FBENGCVQLDKVAT-VPZFWCOMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-(5-iodo-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• IUPAC Traditional name: [(2R,4R,5R)-3-(benzoyloxy)-4-fluoro-5-(5-iodo-2,4-dioxo-3H-pyrimidin-1-yl)oxolan-2-yl]methyl benzoate
• Synonyms: 3',5'-Di-O-benzoyl Fialuridine; 3’,5’-Di-O-benzoyl-1-(2-deoxy-2-fluoro-D-arabinofuranosyl)-5-iodo-2,4(1H,3H)-pyrimidinedione; 3’,5’-Di-O-benzoyl-1-(2'-deoxy-2'-fluoro-D-arabinofuranosyl)-5-iodouracil; 3',5'-Di-O-benzoyl Fialuridine (1:3 α/β Mixture)(see D417160)

Database IDs

• CAS Number: 97614-45-4
• PubChem SID: 162261011
• PubChem CID: 71315918

CALCULATED PROPERTIES

• Acid pKa: 7.8011556
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.449994
• LogD (pH = 7.4): 4.308885
• Log P: 4.4521346
• Molar Refractivity: 123.8665 cm^3
• Polarizability: 48.111454 Å^3
• Polar Surface Area: 111.24 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - D417160

Fialuridine intermediate.

Toronto Research Chemicals - D417150

Fialuridine intermediate.