(2R,3R,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-(4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-3-yl benzoate

• ChemBase ID: 178918
• Molecular Formular: C30H24N2O8S
• Molecular Mass: 572.58516
• Monoisotopic Mass: 572.12533674
• SMILES: [C@@H]1([C@H]([C@@H](O[C@@H]1COC(=O)c1ccccc1)n1c(=S)[nH]c(=O)cc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: O=c1ccn(c(=S)[nH]1)[C@@H]1O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C30H24N2O8S/c33-23-16-17-32(30(41)31-23)26-25(40-29(36)21-14-8-3-9-15-21)24(39-28(35)20-12-6-2-7-13-20)22(38-26)18-37-27(34)19-10-4-1-5-11-19/h1-17,22,24-26H,18H2,(H,31,33,41)/t22-,24-,25-,26-/m1/s1
• InChIKey: ZAHOZJCQNRXDIV-VNSJUHMKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-(4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-3-yl benzoate
• IUPAC Traditional name: (2R,3R,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-(4-oxo-2-sulfanylidene-3H-pyrimidin-1-yl)oxolan-3-yl benzoate
• Synonyms: 2-Thio-uridine 2',3',5'-Tribenzoate; 2-Thiouridine 2',3',5'-Tribenzoate; 2',3',5'-Tri-O-benzoyl-2-thiouridine

Database IDs

• CAS Number: 21052-18-6
• PubChem SID: 164234828
• PubChem CID: 13830034

CALCULATED PROPERTIES

• Acid pKa: 8.010338
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.9592032
• LogD (pH = 7.4): 5.866473
• Log P: 5.960527
• Molar Refractivity: 150.0225 cm^3
• Polarizability: 58.642273 Å^3
• Polar Surface Area: 120.47 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - T771500

Protected 2-Thiouridine.

REFERENCES

• El-Tayeb, A., et al.: J. Med. Chem., 49, 7076 (2006)