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

• ChemBase ID: 163409
• Molecular Formular: C34H40N2O6Si
• Molecular Mass: 600.7767
• Monoisotopic Mass: 600.26556354
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1ccc(=O)[nH]c1=O)COC(c1ccccc1)(c1ccccc1)c1ccccc1)O)O[Si](C)(C)C(C)(C)C
• Canonical SMILES: O[C@@H]1[C@@H](COC(c2ccccc2)(c2ccccc2)c2ccccc2)O[C@H]([C@@H]1O[Si](C(C)(C)C)(C)C)n1ccc(=O)[nH]c1=O
• InChI: InChI=1S/C34H40N2O6Si/c1-33(2,3)43(4,5)42-30-29(38)27(41-31(30)36-22-21-28(37)35-32(36)39)23-40-34(24-15-9-6-10-16-24,25-17-11-7-12-18-25)26-19-13-8-14-20-26/h6-22,27,29-31,38H,23H2,1-5H3,(H,35,37,39)/t27-,29-,30-,31-/m1/s1
• InChIKey: XOHRAGVYVNTJQV-PMFUCWTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(2R,3R,4R,5R)-3-[(tert-butyldimethylsilyl)oxy]-4-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione
• IUPAC Traditional name: 1-[(2R,3R,4R,5R)-3-[(tert-butyldimethylsilyl)oxy]-4-hydroxy-5-[(triphenylmethoxy)methyl]oxolan-2-yl]-3H-pyrimidine-2,4-dione
• Synonyms: 2'-O-[(1,1-Dimethylethyl)dimethylsilyl]-5'-O-(triphenylmethyl)urdine; 2'-O-(tert-Butyldimethylsilyl)-5'-O-trityluridine

Database IDs

• CAS Number: 117136-35-3
• PubChem SID: 162257544
• PubChem CID: 14034383

CALCULATED PROPERTIES

• Acid pKa: 9.701199
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 6.3871727
• LogD (pH = 7.4): 6.3850503
• Log P: 6.3872
• Molar Refractivity: 162.2151 cm^3
• Polarizability: 65.31282 Å^3
• Polar Surface Area: 97.33 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 181-183°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B691710

A protected potential anti-cancer and anti-viral agent.

REFERENCES

• Lin, T-S., et al.: J. Med. Chem., 34, 693 (1991)