9-[(2R,3R,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-2-chloro-9H-purin-6-amine

• ChemBase ID: 164719
• Molecular Formular: C28H54ClN5O4Si3
• Molecular Mass: 644.46896
• Monoisotopic Mass: 643.31721251
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)Cl)N)CO[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C
• Canonical SMILES: Clc1nc(N)c2c(n1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O[Si](C(C)(C)C)(C)C)O[Si](C(C)(C)C)(C)C)CO[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C28H54ClN5O4Si3/c1-26(2,3)39(10,11)35-16-18-20(37-40(12,13)27(4,5)6)21(38-41(14,15)28(7,8)9)24(36-18)34-17-31-19-22(30)32-25(29)33-23(19)34/h17-18,20-21,24H,16H2,1-15H3,(H2,30,32,33)/t18-,20-,21-,24-/m1/s1
• InChIKey: RKPWDVVMCBUEMP-UMCMBGNQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,3R,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-2-chloro-9H-purin-6-amine
• IUPAC Traditional name: 9-[(2R,3R,4R,5R)-3,4-bis[(tert-butyldimethylsilyl)oxy]-5-{[(tert-butyldimethylsilyl)oxy]methyl}oxolan-2-yl]-2-chloropurin-6-amine
• Synonyms: 2-Chloro-2',3',5'-tris-O-[(1,1-dimethylethyl)dimethylsilyl]-adenosine

Database IDs

• CAS Number: 195727-26-5
• PubChem SID: 162258854
• PubChem CID: 10746748

CALCULATED PROPERTIES

• Acid pKa: 18.082539
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 7.1431937
• LogD (pH = 7.4): 7.1432
• Log P: 7.1432
• Molar Refractivity: 158.2385 cm^3
• Polarizability: 68.56775 Å^3
• Polar Surface Area: 106.54 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Methoxide; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - C427900

A protected A1-adenosine receptor agonist. Induces apoptosis.

REFERENCES

• Evans, et al.: Neurosci. Lett., 83, 287 (1987)
• Szondy, Z.: Biochem. J., 304, 877 (1994)