[(2S)-6-(acetyloxy)-5-oxo-5,6-dihydro-2H-pyran-2-yl]methyl acetate

• ChemBase ID: 166771
• Molecular Formular: C10H12O6
• Molecular Mass: 228.19868
• Monoisotopic Mass: 228.0633881
• SMILES: C1=CC(=O)C(O[C@H]1COC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1C=CC(=O)C(O1)OC(=O)C
• InChI: InChI=1S/C10H12O6/c1-6(11)14-5-8-3-4-9(13)10(16-8)15-7(2)12/h3-4,8,10H,5H2,1-2H3/t8-,10?/m0/s1
• InChIKey: WEOSGCBXZQXDBQ-PEHGTWAWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S)-6-(acetyloxy)-5-oxo-5,6-dihydro-2H-pyran-2-yl]methyl acetate
• IUPAC Traditional name: [(2S)-6-(acetyloxy)-5-oxo-2,6-dihydropyran-2-yl]methyl acetate
• Synonyms: 2-(Acetyloxy)-6-[(acetyloxy)methyl]-2H-pyran-3(6H)-one; 1,6-Diacetyl 3,4-DGE; 1,6-Diacetyl 3,4-Dideoxyglucosone-3-ene

Database IDs

• PubChem SID: 162260904
• PubChem CID: 71315872

CALCULATED PROPERTIES

• Acid pKa: 17.485952
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.27606836
• LogD (pH = 7.4): 0.27606836
• Log P: 0.27606836
• Molar Refractivity: 51.9467 cm^3
• Polarizability: 20.66036 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D327005

An intermediate for immunosuppressants useful for treatment of chronic rheumatoid arthritis and autoimmune disease.

REFERENCES

• Shafizadeh, F., et al.: Carbohydr. Res., 71, 169 (1979)