methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[3-(acetyloxy)-5-iodophenoxy]oxane-2-carboxylate

• ChemBase ID: 159013
• Molecular Formular: C21H23IO12
• Molecular Mass: 594.30459
• Monoisotopic Mass: 594.02342418
• SMILES: O1[C@@H]([C@@H]([C@@H]([C@H]([C@H]1C(=O)OC)OC(=O)C)OC(=O)C)OC(=O)C)Oc1cc(cc(c1)OC(=O)C)I
• Canonical SMILES: COC(=O)[C@H]1O[C@H](Oc2cc(I)cc(c2)OC(=O)C)[C@@H]([C@@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H23IO12/c1-9(23)29-14-6-13(22)7-15(8-14)33-21-19(32-12(4)26)17(31-11(3)25)16(30-10(2)24)18(34-21)20(27)28-5/h6-8,16-19,21H,1-5H3/t16-,17-,18-,19+,21+/m1/s1
• InChIKey: HHCLYQKBEARFJZ-TYZHSBRISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[3-(acetyloxy)-5-iodophenoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,3R,4R,5S,6R)-3,4,5-tris(acetyloxy)-6-[3-(acetyloxy)-5-iodophenoxy]oxane-2-carboxylate
• Synonyms: 3-(Acetyloxy)-5-iodophenyl-β-D-glucopyranosiduronic Acid Methyl Ester Triacetate; 3-(Acetyloxy)-5-iodophenol-2',3',4'-tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 490028-21-2
• PubChem SID: 162253148
• PubChem CID: 71312772

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.7273626
• LogD (pH = 7.4): 1.7273626
• Log P: 1.7273626
• Molar Refractivity: 116.7692 cm^3
• Polarizability: 48.11473 Å^3
• Polar Surface Area: 149.96 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A166000

Intermediate for the synthesis of glucuronide conjugates of trans-Resveratrol

REFERENCES

• Learmonth, D.A., et al.: Bioconjug. Chem., 14, 262 (2003)