methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{2-[(benzyloxy)carbonyl]phenoxy}oxane-2-carboxylate

• ChemBase ID: 173380
• Molecular Formular: C27H28O12
• Molecular Mass: 544.50402
• Monoisotopic Mass: 544.15807634
• 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)OCc1ccccc1
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Oc2ccccc2C(=O)OCc2ccccc2)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C27H28O12/c1-15(28)35-21-22(36-16(2)29)24(37-17(3)30)27(39-23(21)26(32)33-4)38-20-13-9-8-12-19(20)25(31)34-14-18-10-6-5-7-11-18/h5-13,21-24,27H,14H2,1-4H3/t21-,22-,23-,24+,27+/m1/s1
• InChIKey: GSTDLQNCIWASGN-AHPXAKOISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{2-[(benzyloxy)carbonyl]phenoxy}oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-{2-[(benzyloxy)carbonyl]phenoxy}oxane-2-carboxylate
• Synonyms: 2-[(Phenylmethoxy)carbonyl]phenyl β-D-Glucopyranosiduronic Acid Methyl Ester Triacetate; Methyl 1-((2-Benzyloxycarbonxyl)phenyl)-2,3,4-tri-O-acetyl-β-D-glucopyranuronate

Database IDs

• CAS Number: 221287-88-3
• PubChem SID: 164229290
• PubChem CID: 71750224

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 2.9191072
• LogD (pH = 7.4): 2.9191072
• Log P: 2.9191072
• Molar Refractivity: 128.9122 cm^3
• Polarizability: 52.193085 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether
• Apperance: White Powder
• Melting Point: 131-135°C

DETAILS

Toronto Research Chemicals - M292775

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)