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

• ChemBase ID: 162416
• Molecular Formular: C21H40N2O5Si2
• Molecular Mass: 456.7237
• Monoisotopic Mass: 456.24757545
• SMILES: C1(O[Si](C(C)(C)C)(C)C)[C@@H](CO[Si](C(C)(C)C)(C)C)O[C@@H](n2ccc(=O)[nH]c2=O)C1
• Canonical SMILES: O=c1ccn(c(=O)[nH]1)[C@H]1CC([C@H](O1)CO[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C21H40N2O5Si2/c1-20(2,3)29(7,8)26-14-16-15(28-30(9,10)21(4,5)6)13-18(27-16)23-12-11-17(24)22-19(23)25/h11-12,15-16,18H,13-14H2,1-10H3,(H,22,24,25)/t15?,16-,18-/m1/s1
• InChIKey: DKEAALKCPSPQCU-WOEZKJSCSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 64911-18-8
• PubChem SID: 162256551
• PubChem CID: 46780844

CALCULATED PROPERTIES

• Acid pKa: 9.705758
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.4508734
• LogD (pH = 7.4): 4.448773
• Log P: 4.4509
• Molar Refractivity: 110.7511 cm^3
• Polarizability: 48.11564 Å^3
• Polar Surface Area: 77.1 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - B585360

An intermediate in the preparation of cytidine derivatives

REFERENCES

• Zhang, W., et al.: Chem. Res. Toxicol., 8, 148 (1995)