2-amino-9-[(1S,3R,4R)-4-(benzyloxy)-3-[(benzyloxy)methyl]-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 166899
• Molecular Formular: C26H27N5O3
• Molecular Mass: 457.52428
• Monoisotopic Mass: 457.21138975
• SMILES: [nH]1c(nc2c(c1=O)ncn2[C@H]1C[C@H]([C@H](C1=C)COCc1ccccc1)OCc1ccccc1)N
• Canonical SMILES: Nc1[nH]c(=O)c2c(n1)n(cn2)[C@H]1C[C@H]([C@H](C1=C)COCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C26H27N5O3/c1-17-20(15-33-13-18-8-4-2-5-9-18)22(34-14-19-10-6-3-7-11-19)12-21(17)31-16-28-23-24(31)29-26(27)30-25(23)32/h2-11,16,20-22H,1,12-15H2,(H3,27,29,30,32)/t20-,21-,22+/m0/s1
• InChIKey: KROVOOOAPHSWCR-FDFHNCONSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(1S,3R,4R)-4-(benzyloxy)-3-[(benzyloxy)methyl]-2-methylidenecyclopentyl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: 2-amino-9-[(1S,3R,4R)-4-(benzyloxy)-3-[(benzyloxy)methyl]-2-methylidenecyclopentyl]-1H-purin-6-one
• Synonyms: 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-2-methylene-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]-6H-purin-6-one; [1S-(1α,3α,4β)]-2-Amino-1,9-dihydro-9-[2-methylene-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]cyclopentyl]-6H-purin-6-one; 3',5'-Di-O-benzyl Entecavir

Database IDs

• CAS Number: 142217-81-0
• PubChem SID: 162261032
• PubChem CID: 71315926

CALCULATED PROPERTIES

• Acid pKa: 10.166993
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.7728465
• LogD (pH = 7.4): 2.772274
• Log P: 2.7729292
• Molar Refractivity: 130.1618 cm^3
• Polarizability: 49.11658 Å^3
• Polar Surface Area: 103.76 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D417550

3’,5’-Di-O-benzyl Entecavir is an intermediate in the preparation of the hepatitis B antiviral agent, Entecavir (E558900).

REFERENCES

• Li, R. et al.: Zhong. Yao., 6, 292 (2008)
• Bisacchi, G.S. et al.: Bioorg. Med. Chem. Lett., 7, 127 (2008)