2-{[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}benzoic acid

• ChemBase ID: 173444
• Molecular Formular: C20H22O12
• Molecular Mass: 454.38148
• Monoisotopic Mass: 454.11112614
• SMILES: c1c(c(ccc1)O[C@H]1O[C@@H]([C@@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)C(=O)O
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Oc2ccccc2C(=O)O)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C20H22O12/c1-9(21)28-14-15(29-10(2)22)17(30-11(3)23)20(32-16(14)19(26)27-4)31-13-8-6-5-7-12(13)18(24)25/h5-8,14-17,20H,1-4H3,(H,24,25)/t14-,15-,16-,17+,20+/m1/s1
• InChIKey: OYMYHWWBEZVDAQ-PANQXIRQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}benzoic acid
• IUPAC Traditional name: 2-{[(2R,3S,4R,5R,6R)-3,4,5-tris(acetyloxy)-6-(methoxycarbonyl)oxan-2-yl]oxy}benzoic acid
• Synonyms: 2-Carboxyphenyl β-D-Glucopyranosiduronic Acid 6-Methyl Ester Triacetate; Methyl 1-(2-Carboxyphenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

Database IDs

• CAS Number: 221287-90-7
• PubChem SID: 164229354
• PubChem CID: 71750251

CALCULATED PROPERTIES

• Acid pKa: 3.6509178
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.9974744
• LogD (pH = 7.4): -2.4758458
• Log P: 0.84874016
• Molar Refractivity: 99.5305 cm^3
• Polarizability: 40.693615 Å^3
• Polar Surface Area: 160.96 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - M294443

An intermediate in the synthesis of the metabolite of Nitazoxanide.

REFERENCES

• Honma, K., et al.: Chem. Pharm. Bull., 24, 394 (1976)
• Dubreuil, L., et al.: Antimicrob. Agents Chemother., 40, 2266 (1976)
• Stockis, A., et al.: Int. J. Clin. Pharmacol. Ther., 34, 349 (1976)