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

• ChemBase ID: 166033
• Molecular Formular: C28H26N2O5
• Molecular Mass: 470.51644
• Monoisotopic Mass: 470.18417194
• SMILES: [C@H]1(C[C@H](O[C@H]1n1c(=O)[nH]c(=O)cc1)COC(c1ccccc1)(c1ccccc1)c1ccccc1)O
• Canonical SMILES: O[C@@H]1C[C@H](O[C@H]1n1ccc(=O)[nH]c1=O)COC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C28H26N2O5/c31-24-18-23(35-26(24)30-17-16-25(32)29-27(30)33)19-34-28(20-10-4-1-5-11-20,21-12-6-2-7-13-21)22-14-8-3-9-15-22/h1-17,23-24,26,31H,18-19H2,(H,29,32,33)/t23-,24+,26+/m0/s1
• InChIKey: SERBFLXSXXCIFH-BFLUCZKCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,5S)-3-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,5S)-3-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 3'-Deoxy-5'-O-(triphenylmethyl)uridine; 3'-Deoxy-5'-O-trityl Uridine

Database IDs

• CAS Number: 161110-05-0
• PubChem SID: 162260166
• PubChem CID: 10906787

CALCULATED PROPERTIES

• Acid pKa: 9.701476
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.075107
• LogD (pH = 7.4): 4.072995
• Log P: 4.0751343
• Molar Refractivity: 131.2699 cm^3
• Polarizability: 50.63691 Å^3
• Polar Surface Area: 88.1 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol
• Apperance: White Crystalline Solid
• Melting Point: 82-88°C

DETAILS

Toronto Research Chemicals - D287850

A protected potential anti-cancer and anti-viral agent.

REFERENCES

• Lin, T-S., et al.: J. Med. Chem., 34, 693 (1991)