1-[(1S,2R,4R,5S)-4-[(triphenylmethoxy)methyl]-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 179347
• Molecular Formular: C28H24N2O5
• Molecular Mass: 468.50056
• Monoisotopic Mass: 468.16852188
• SMILES: n1([C@H]2[C@H]3[C@@H]([C@H](O2)COC(c2ccccc2)(c2ccccc2)c2ccccc2)O3)ccc(=O)[nH]c1=O
• Canonical SMILES: O=c1ccn(c(=O)[nH]1)[C@@H]1O[C@@H]([C@@H]2[C@H]1O2)COC(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C28H24N2O5/c31-23-16-17-30(27(32)29-23)26-25-24(35-25)22(34-26)18-33-28(19-10-4-1-5-11-19,20-12-6-2-7-13-20)21-14-8-3-9-15-21/h1-17,22,24-26H,18H2,(H,29,31,32)/t22-,24+,25+,26-/m1/s1
• InChIKey: LASYVDMYFAPCBP-HMNRDNJPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(1S,2R,4R,5S)-4-[(triphenylmethoxy)methyl]-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(1S,2R,4R,5S)-4-[(triphenylmethoxy)methyl]-3,6-dioxabicyclo[3.1.0]hexan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 5'-O-Trityluridine-2',3'-lyxo-epoxide; 1-[2,3-Anhydro-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione

Database IDs

• CAS Number: 96253-10-0
• PubChem SID: 164235257
• PubChem CID: 11762421

CALCULATED PROPERTIES

• Acid pKa: 9.701333
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.546516
• LogD (pH = 7.4): 4.544403
• Log P: 4.546543
• Molar Refractivity: 128.8569 cm^3
• Polarizability: 49.98279 Å^3
• Polar Surface Area: 77.1 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - T890510

Synthetic intermediate used to synthesize a variety of antiviral agents

REFERENCES

• Bamford, M.J., et al.: J. Med. Chem., 33, 2494 (1990)