5-bromo-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: 162415
• Molecular Formular: C21H39BrN2O5Si2
• Molecular Mass: 535.61976
• Monoisotopic Mass: 534.15808742
• SMILES: C1(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)Br)C1
• Canonical SMILES: O=c1[nH]c(=O)n(cc1Br)[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/C21H39BrN2O5Si2/c1-20(2,3)30(7,8)27-13-16-15(29-31(9,10)21(4,5)6)11-17(28-16)24-12-14(22)18(25)23-19(24)26/h12,15-17H,11,13H2,1-10H3,(H,23,25,26)/t15?,16-,17-/m1/s1
• InChIKey: XZYGEGFEDTXIDM-YJEKIOLLSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 154925-95-8
• PubChem SID: 162256550
• PubChem CID: 46780843

CALCULATED PROPERTIES

• Acid pKa: 8.040326
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.440759
• LogD (pH = 7.4): 5.353194
• Log P: 5.442
• Molar Refractivity: 118.3604 cm^3
• Polarizability: 50.886852 Å^3
• Polar Surface Area: 77.1 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 142-144°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - B585340

An intermediate in the preparation of cytidine derivatives