benzyl (3S,5S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate

• ChemBase ID: 161608
• Molecular Formular: C13H16O7
• Molecular Mass: 284.26194
• Monoisotopic Mass: 284.08960285
• SMILES: O1C([C@@H](C([C@@H](C1C(=O)OCc1ccccc1)O)O)O)O
• Canonical SMILES: OC1OC(C(=O)OCc2ccccc2)[C@H](C([C@H]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
• InChIKey: MYEUFSLWFIOAGY-SJZSRGDHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (3S,5S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• IUPAC Traditional name: benzyl (3S,5S)-3,4,5,6-tetrahydroxyoxane-2-carboxylate
• Synonyms: Glucuronic Acid Benzyl Ester; D-Glucuronic Acid Phenylmethyl Ester; Benzyl D-Glucuronate

Database IDs

• CAS Number: 135970-30-8
• PubChem SID: 162255743
• PubChem CID: 45038287

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

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 104-108°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B279800

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

REFERENCES

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