[(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[6-oxo-2-(phenylamino)-6,9-dihydro-1H-purin-9-yl]oxolan-2-yl]methyl acetate

• ChemBase ID: 176578
• Molecular Formular: C22H23N5O8
• Molecular Mass: 485.44672
• Monoisotopic Mass: 485.15466272
• SMILES: n1([C@H]2[C@@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)cnc2c1nc([nH]c2=O)Nc1ccccc1
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC(=O)C)[C@H](O[C@H]1n1cnc2c1nc(Nc1ccccc1)[nH]c2=O)COC(=O)C
• InChI: InChI=1S/C22H23N5O8/c1-11(28)32-9-15-17(33-12(2)29)18(34-13(3)30)21(35-15)27-10-23-16-19(27)25-22(26-20(16)31)24-14-7-5-4-6-8-14/h4-8,10,15,17-18,21H,9H2,1-3H3,(H2,24,25,26,31)/t15-,17-,18-,21-/m1/s1
• InChIKey: HGLBYLIJQHKWHL-QTQZEZTPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[6-oxo-2-(phenylamino)-6,9-dihydro-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4-bis(acetyloxy)-5-[6-oxo-2-(phenylamino)-1H-purin-9-yl]oxolan-2-yl]methyl acetate
• Synonyms: 2',3',5'-Tri-O-acetyl-2-N-penylguanosine; N-Phenyl Guanosine 2',3',5'-Triacetate

Database IDs

• CAS Number: 53296-13-2
• PubChem SID: 164232488
• PubChem CID: 12877526

CALCULATED PROPERTIES

• Acid pKa: 9.422105
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.8011859
• LogD (pH = 7.4): 0.7975985
• Log P: 0.80123585
• Molar Refractivity: 118.4086 cm^3
• Polarizability: 45.31599 Å^3
• Polar Surface Area: 159.44 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Dimethyl Sulfoxide; Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - P327580

Used in the synthesis of C-2 substituted adenosines.

REFERENCES

• Trivedi, B.: Nucleos. Nucleot. 7, 393 (1988)
• Trivedi, B. et al.: J. Med. Chem. 32, 1667 (1989).