[(2R,3S,5R)-3-(acetyloxy)-5-[2-amino-6-(benzyloxy)-9H-purin-9-yl]oxolan-2-yl]methyl acetate

• ChemBase ID: 166753
• Molecular Formular: C21H23N5O6
• Molecular Mass: 441.43722
• Monoisotopic Mass: 441.16483348
• SMILES: n1c(nc2c(c1OCc1ccccc1)ncn2[C@H]1C[C@@H]([C@H](O1)COC(=O)C)OC(=O)C)N
• Canonical SMILES: CC(=O)O[C@H]1C[C@@H](O[C@@H]1COC(=O)C)n1cnc2c1nc(N)nc2OCc1ccccc1
• InChI: InChI=1S/C21H23N5O6/c1-12(27)29-10-16-15(31-13(2)28)8-17(32-16)26-11-23-18-19(26)24-21(22)25-20(18)30-9-14-6-4-3-5-7-14/h3-7,11,15-17H,8-10H2,1-2H3,(H2,22,24,25)/t15-,16+,17+/m0/s1
• InChIKey: QLUZVLZNJMLEJA-GVDBMIGSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,5R)-3-(acetyloxy)-5-[2-amino-6-(benzyloxy)-9H-purin-9-yl]oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,5R)-3-(acetyloxy)-5-[2-amino-6-(benzyloxy)purin-9-yl]oxolan-2-yl]methyl acetate
• Synonyms: 2'-Deoxy-6-O-(phenylmethyl)guanosine 3',5'-Diacetate; 3',5'-Di-O-acetyl O6-Benzyl-2'-deoxyguanosine

Database IDs

• CAS Number: 144640-75-5
• PubChem SID: 162260886
• PubChem CID: 71315866

CALCULATED PROPERTIES

• Acid pKa: 16.211061
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 1.9375043
• LogD (pH = 7.4): 1.9375128
• Log P: 1.9375129
• Molar Refractivity: 111.0097 cm^3
• Polarizability: 43.622055 Å^3
• Polar Surface Area: 140.68 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Solid

DETAILS

Toronto Research Chemicals - D309200

Protected Deoxyguanosine.

REFERENCES

• Wei, G., et al.: J. Med. Chem., 48, 256 (2005)