1-[(2R,4R,5R)-4-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-5-(2H3)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 179326
• Molecular Formular: C29H28N2O5
• Molecular Mass: 484.54302
• Monoisotopic Mass: 484.19982201
• SMILES: [C@@H]1(C[C@@H](O[C@@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)n1c(=O)[nH]c(=O)c(c1)C)O
• Canonical SMILES: O[C@H]1C[C@@H](O[C@@H]1COC(c1ccccc1)(c1ccccc1)c1ccccc1)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C29H28N2O5/c1-20-18-31(28(34)30-27(20)33)26-17-24(32)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/h2-16,18,24-26,32H,17,19H2,1H3,(H,30,33,34)/t24-,25-,26-/m1/s1
• InChIKey: FZDHVUVGQXVYOP-TWJOJJKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4R,5R)-4-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-5-(^2H₃)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4R,5R)-4-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-5-(^2H₃)methyl-3H-pyrimidine-2,4-dione
• Synonyms: 1-[2-Deoxy-5-O-(triphenylmethyl)-β-D-threo-pentofuranosyl]-5-methyl-2,4(1H,3H)-pyrimidinedione-d3; 1-(2-Deoxy-5-O-trityl-β-D-threo-pentofuranosyl)thymine-d3; 5'-O-Trityl-3'-β-hydroxythymidine-d3

Database IDs

• PubChem SID: 164235236
• PubChem CID: 71752867

CALCULATED PROPERTIES

• Acid pKa: 9.960286
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 4.681013
• LogD (pH = 7.4): 4.679848
• Log P: 4.681028
• Molar Refractivity: 135.2134 cm^3
• Polarizability: 52.477596 Å^3
• Polar Surface Area: 88.1 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T887952

An intermediate in the preparation of labelled thymidine monophosphate analogues

REFERENCES

• Vanheusden, V., et al.: Bioorg. Med. Chem. Lett., 12, 2695 (2002)