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

• ChemBase ID: 179346
• Molecular Formular: C28H26N2O6
• Molecular Mass: 486.51584
• Monoisotopic Mass: 486.17908656
• SMILES: n1([C@H]2[C@@H]([C@@H]([C@H](O2)COC(c2ccccc2)(c2ccccc2)c2ccccc2)O)O)ccc(=O)[nH]c1=O
• Canonical SMILES: O[C@@H]1[C@@H](COC(c2ccccc2)(c2ccccc2)c2ccccc2)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C28H26N2O6/c31-23-16-17-30(27(34)29-23)26-25(33)24(32)22(36-26)18-35-28(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-17,22,24-26,32-33H,18H2,(H,29,31,34)/t22-,24-,25-,26-/m1/s1
• InChIKey: YQHCGMPQZCIQPS-VNSJUHMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 5'-O-Triphenylmethyluridine; NSC 97038; 5'-O-Trityl Uridine

Database IDs

• CAS Number: 6554-10-5
• PubChem SID: 164235256
• PubChem CID: 7568287

CALCULATED PROPERTIES

• Acid pKa: 9.700746
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 3.3848124
• LogD (pH = 7.4): 3.3826969
• Log P: 3.3848395
• Molar Refractivity: 132.367 cm^3
• Polarizability: 51.26764 Å^3
• Polar Surface Area: 108.33 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 175-176°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T890500

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

REFERENCES

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