1-[(2R,4R,5R)-4-fluoro-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 179313
• Molecular Formular: C29H27FN2O4
• Molecular Mass: 486.5340832
• Monoisotopic Mass: 486.19548557
• SMILES: [C@H]1(C[C@@H](O[C@@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)n1c(=O)[nH]c(=O)c(c1)C)F
• Canonical SMILES: F[C@@H]1C[C@@H](O[C@@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C29H27FN2O4/c1-20-18-32(28(34)31-27(20)33)26-17-24(30)25(36-26)19-35-29(21-11-5-2-6-12-21,22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,18,24-26H,17,19H2,1H3,(H,31,33,34)/t24-,25-,26-/m1/s1
• InChIKey: GFDJOSNZNLVRCL-TWJOJJKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-fluoro-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-5-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-fluoro-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-5-methyl-3H-pyrimidine-2,4-dione
• Synonyms: 5-O-Trityl-3'-deoxy-3'-fluorothymidine; 3'-Deoxy-3'-fluoro-5'-O-(triphenylmethyl)thymidine

Database IDs

• CAS Number: 135197-63-6
• PubChem SID: 164235223
• PubChem CID: 29987836

CALCULATED PROPERTIES

• Acid pKa: 9.710312
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.5720935
• LogD (pH = 7.4): 5.5700235
• Log P: 5.5721197
• Molar Refractivity: 133.5213 cm^3
• Polarizability: 51.544643 Å^3
• Polar Surface Area: 67.87 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T887675

An intermediate in the preparation of thymidine monophosphate analogues

REFERENCES

• Cheng, Y., et al.: J. Biol. Chem., 262, 2187 (1987)
• Shields, A., et al.: Nature Med., 4, 1334 (1987)