(1R,2S,6S,9R)-6-{[(azidosulfonyl)oxy]methyl}-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecane

• ChemBase ID: 178744
• Molecular Formular: C12H19N3O8S
• Molecular Mass: 365.35956
• Monoisotopic Mass: 365.08928558
• SMILES: C1[C@@H]2[C@H]([C@H]3[C@@](O1)(OC(O3)(C)C)COS(=O)(=O)N=[N+]=[N-])OC(O2)(C)C
• Canonical SMILES: [N-]=[N+]=NS(=O)(=O)OC[C@]12OC[C@@H]3[C@H]([C@@H]2OC(O1)(C)C)OC(O3)(C)C
• InChI: InChI=1S/C12H19N3O8S/c1-10(2)20-7-5-18-12(6-19-24(16,17)15-14-13)9(8(7)21-10)22-11(3,4)23-12/h7-9H,5-6H2,1-4H3/t7-,8-,9+,12+/m1/s1
• InChIKey: ULLWHTAOFMDWSA-XBWDGYHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,6S,9R)-6-{[(azidosulfonyl)oxy]methyl}-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^2,^6]dodecane
• IUPAC Traditional name: (1R,2S,6S,9R)-6-{[(azidosulfonyl)oxy]methyl}-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.0^2,^6]dodecane
• Synonyms: 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose Azidosulfate; Topiramate Azidosulfate

Database IDs

• CAS Number: 106881-35-0
• PubChem SID: 164234654
• PubChem CID: 13785066

CALCULATED PROPERTIES

• H Acceptors: 9
• H Donor: 0
• LogD (pH = 5.5): 0.6577987
• LogD (pH = 7.4): 0.6577987
• Log P: 0.7718443
• Molar Refractivity: 76.8591 cm^3
• Polarizability: 31.677752 Å^3
• Polar Surface Area: 118.95 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - T540260

Topiramate (T540250) impurity.

REFERENCES

• Maryanoff, B.E., et al.: J. Med. Chem., 30, 880 (1987)