1-[(2R,4S,5R)-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-5-(2H3)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 174359
• Molecular Formular: C11H16N2O5
• Molecular Mass: 256.25514
• Monoisotopic Mass: 256.10592162
• SMILES: [nH]1c(=O)c(cn(c1=O)[C@H]1C[C@@H]([C@H](O1)CO)OC)C
• Canonical SMILES: CO[C@H]1C[C@@H](O[C@@H]1CO)n1cc(C)c(=O)[nH]c1=O
• InChI: InChI=1S/C11H16N2O5/c1-6-4-13(11(16)12-10(6)15)9-3-7(17-2)8(5-14)18-9/h4,7-9,14H,3,5H2,1-2H3,(H,12,15,16)/t7-,8+,9+/m0/s1
• InChIKey: ZGBKEOLAPVBJFC-DJLDLDEBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-5-(^2H₃)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4S,5R)-5-(hydroxymethyl)-4-methoxyoxolan-2-yl]-5-(^2H₃)methyl-3H-pyrimidine-2,4-dione
• Synonyms: 3’-Methoxy-3’-deoxythymidine-d3; 3'-O-Methyl Thymidine-d3

Database IDs

• PubChem SID: 164230269
• PubChem CID: 71750617

CALCULATED PROPERTIES

• Acid pKa: 9.960317
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -0.47594196
• LogD (pH = 7.4): -0.47710708
• Log P: -0.47592708
• Molar Refractivity: 60.1632 cm^3
• Polarizability: 23.883001 Å^3
• Polar Surface Area: 88.1 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Blue Solid

DETAILS

Toronto Research Chemicals - M330747

An intermediate in the preparation of anti-HIV pharmaceuticals

REFERENCES

• Jie, L., et al.: J. Med. Chem., 33, 2481 (1990)
• McGuigan, C., et al.: Bioorg. Med. Chem. Lett., 3, 1207 (1990)