(2S,3R,4R,5R,6R)-4-(benzoyloxy)-6-[(benzoyloxy)methyl]-5-chloro-2-methoxyoxan-3-yl benzoate

• ChemBase ID: 173452
• Molecular Formular: C28H25ClO8
• Molecular Mass: 524.9463
• Monoisotopic Mass: 524.12379544
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)c1ccccc1)OC)OC(=O)c1ccccc1)OC(=O)c1ccccc1)Cl
• Canonical SMILES: CO[C@H]1O[C@@H](COC(=O)c2ccccc2)[C@H]([C@@H]([C@@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)Cl
• InChI: InChI=1S/C28H25ClO8/c1-33-28-24(37-27(32)20-15-9-4-10-16-20)23(36-26(31)19-13-7-3-8-14-19)22(29)21(35-28)17-34-25(30)18-11-5-2-6-12-18/h2-16,21-24,28H,17H2,1H3/t21-,22-,23+,24-,28+/m1/s1
• InChIKey: UEIVKNTXZOYDEL-NRUNVSGISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R,6R)-4-(benzoyloxy)-6-[(benzoyloxy)methyl]-5-chloro-2-methoxyoxan-3-yl benzoate
• IUPAC Traditional name: (2S,3R,4R,5R,6R)-4-(benzoyloxy)-6-[(benzoyloxy)methyl]-5-chloro-2-methoxyoxan-3-yl benzoate
• Synonyms: Methyl 2,3,6-Tri-O-benzoyl-4-chloro-4-deoxy-α-D-glucopyranoside; Methyl 4-Chloro-4-deoxy-α-D-glucopyranoside Tribenzoate

Database IDs

• CAS Number: 41881-07-6
• PubChem SID: 164229362
• PubChem CID: 71750253

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 6.551079
• LogD (pH = 7.4): 6.551079
• Log P: 6.551079
• Molar Refractivity: 133.1916 cm^3
• Polarizability: 52.68675 Å^3
• Polar Surface Area: 97.36 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Brown Solid

DETAILS

Toronto Research Chemicals - M294470

It is used in the investigation of the binding site in glycogen phosphorylase.

REFERENCES

• Street, I.P., et al.: Biochem., 25, 6021 (1986)