1-[(2R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-5-(2H3)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

• ChemBase ID: 162418
• Molecular Formular: C22H42N2O5Si2
• Molecular Mass: 470.75028
• Monoisotopic Mass: 470.26322552
• SMILES: [C@@H]1(O[Si](C(C)(C)C)(C)C)[C@@H](CO[Si](C(C)(C)C)(C)C)O[C@@H](n2cc(c(=O)[nH]c2=O)C)C1
• Canonical SMILES: O=c1[nH]c(=O)n(cc1C)[C@H]1C[C@@H]([C@H](O1)CO[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C22H42N2O5Si2/c1-15-13-24(20(26)23-19(15)25)18-12-16(29-31(10,11)22(5,6)7)17(28-18)14-27-30(8,9)21(2,3)4/h13,16-18H,12,14H2,1-11H3,(H,23,25,26)/t16-,17+,18+/m0/s1
• InChIKey: DDLOCFSZSYGOPG-RCCFBDPRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-5-(^2H₃)methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,4S,5R)-4-[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-5-(^2H₃)methyl-3H-pyrimidine-2,4-dione
• Synonyms: 3',5'-Bis-O-[(1,1-dimethylethyl)dimethylsilyl]thymidine-d3; 3',5'-Bis-O-(tert-butyldimethylsilyl)thymidine-d3

Database IDs

• PubChem SID: 162256553
• PubChem CID: 71314111

CALCULATED PROPERTIES

• Acid pKa: 9.960327
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.728685
• LogD (pH = 7.4): 4.727515
• Log P: 4.7287
• Molar Refractivity: 115.1082 cm^3
• Polarizability: 49.950264 Å^3
• Polar Surface Area: 77.1 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B585382

An intermediate in the preparation of deuterated cytidine derivatives

REFERENCES

• Chamorro, C., et al.: Bioorg. Med. Chem. Lett., 11, 3085 (2001)
• Bornemann, B., et al.: Bioorg. Med. Chem., 14, 6235 (2001)
• Desbouis, D., et al.: J. Med. Chem., 51, 6689 (2001)