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

• ChemBase ID: 171692
• Molecular Formular: C19H21IO10
• Molecular Mass: 536.26851
• Monoisotopic Mass: 536.01794487
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1C(=O)OC)Oc1ccc(cc1)I)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](Oc2ccc(cc2)I)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C19H21IO10/c1-9(21)26-14-15(27-10(2)22)17(28-11(3)23)19(30-16(14)18(24)25-4)29-13-7-5-12(20)6-8-13/h5-8,14-17,19H,1-4H3/t14-,15-,16-,17+,19+/m0/s1
• InChIKey: RSFYKESPVIYVMT-YTGMWSOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-iodophenoxy)oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-(4-iodophenoxy)oxane-2-carboxylate
• Synonyms: 4-Iodophenyl-β-D-glucopyranosiduronic Acid Methyl Ester Triacetate; 4-Iodophenyl 2,3,4-Tri-O-acetyl-β-D-glucuronide Methyl Ester

Database IDs

• CAS Number: 490028-18-7
• PubChem SID: 164227602
• PubChem CID: 71749515

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.1201017
• LogD (pH = 7.4): 2.1201017
• Log P: 2.1201017
• Molar Refractivity: 105.6368 cm^3
• Polarizability: 43.565952 Å^3
• Polar Surface Area: 123.66 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - I718770

Intermediate for the synthesis of glucuronide conjugates of trans-Resveratrol

REFERENCES

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