benzyl (3S,4S)-3,4,5,6-tetrahydroxy(2,3,4,5,6-13C5)oxane-2-carboxylate

• ChemBase ID: 161609
• Molecular Formular: C13H16O7
• Molecular Mass: 290.21786903
• Monoisotopic Mass: 290.10973188
• SMILES: [13C@@H]1([13C@@H]([13CH]([13CH](O[13CH]1[13C](=O)OCc1ccccc1)O)O)O)O
• Canonical SMILES: O[13CH]1O[13CH]([13C](=O)OCc2ccccc2)[13C@H]([13C@@H]([13CH]1O)O)O
• InChI: InChI=1S/C13H16O7/c14-8-9(15)11(20-12(17)10(8)16)13(18)19-6-7-4-2-1-3-5-7/h1-5,8-12,14-17H,6H2/t8-,9-,10?,11?,12?/m0/s1/i8+1,9+1,10+1,11+1,12+1,13+1
• InChIKey: MYEUFSLWFIOAGY-AGSJBGDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (3S,4S)-3,4,5,6-tetrahydroxy(2,3,4,5,6-^1^3C₅)oxane-2-carboxylate
• IUPAC Traditional name: benzyl (3S,4S)-3,4,5,6-tetrahydroxy(2,3,4,5,6-^1^3C₅)oxane-2-carboxylate
• Synonyms: Glucuronic Acid-13C6 Benzyl Ester; D-Glucuronic Acid-13C6 Phenylmethyl Ester; Benzyl D-Glucuronate-13C6

Database IDs

• PubChem SID: 162255744
• PubChem CID: 71313844

CALCULATED PROPERTIES

• Acid pKa: 11.283208
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.74189824
• LogD (pH = 7.4): -0.74195427
• Log P: -0.7418975
• Molar Refractivity: 65.1725 cm^3
• Polarizability: 26.588284 Å^3
• Polar Surface Area: 116.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - B279802

Used in efficient synthesis of 1β-O-acyl glucuronides via regioselective acylation

REFERENCES

• Meng, X., et al.: J. Med. Chem., 50, 6165 (2007)