(4S,5S)-3,4,5-tris(benzoyloxy)-6-[hydroxy(13C)methyl](2,3,4,5,6-13C5)oxan-2-yl benzoate

• ChemBase ID: 178242
• Molecular Formular: C34H28O10
• Molecular Mass: 602.53604903
• Monoisotopic Mass: 602.18837612
• SMILES: [13C@@H]1([13C@@H]([13CH]([13CH](O[13CH]1[13CH2]O)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: O[13CH2][13CH]1O[13CH](OC(=O)c2ccccc2)[13CH]([13C@H]([13C@@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• InChI: InChI=1S/C34H28O10/c35-21-26-27(41-30(36)22-13-5-1-6-14-22)28(42-31(37)23-15-7-2-8-16-23)29(43-32(38)24-17-9-3-10-18-24)34(40-26)44-33(39)25-19-11-4-12-20-25/h1-20,26-29,34-35H,21H2/t26?,27-,28+,29?,34?/m1/s1/i21+1,26+1,27+1,28+1,29+1,34+1
• InChIKey: JSXMRQAFUOMKAD-ATKMHMEMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-3,4,5-tris(benzoyloxy)-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-2-yl benzoate
• IUPAC Traditional name: (4S,5S)-3,4,5-tris(benzoyloxy)-6-[hydroxy(^1^3C)methyl](2,3,4,5,6-^1^3C₅)oxan-2-yl benzoate
• Synonyms: 1,2,3,4-Tetrabenzoate-D-glucopyranose; 1,2,3,4-Tetra-O-benzoyl-D-glucopyranose

Database IDs

• PubChem SID: 164234152
• PubChem CID: 71752404

CALCULATED PROPERTIES

• Acid pKa: 14.581531
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 7.0486603
• LogD (pH = 7.4): 7.0486603
• Log P: 7.0486603
• Molar Refractivity: 155.2114 cm^3
• Polarizability: 61.102337 Å^3
• Polar Surface Area: 134.66 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Light Yellow Solid

DETAILS

Toronto Research Chemicals - T284172

Used in the preparation of α-Glycosphingolipids, important in the innate-type immune response to Gram-negative bacteria.

REFERENCES

• Pilgrim, W. et al.: Org. Lett. 11, 939 (2009).