(2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate

• ChemBase ID: 160675
• Molecular Formular: C12H16O8
• Molecular Mass: 288.25064
• Monoisotopic Mass: 288.08451747
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H]2OC1CO2)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H](OC(=O)C)C2CO[C@@H]([C@H]1OC(=O)C)O2
• InChI: InChI=1S/C12H16O8/c1-5(13)17-9-8-4-16-12(20-8)11(19-7(3)15)10(9)18-6(2)14/h8-12H,4H2,1-3H3/t8?,9-,10+,11-,12-/m1/s1
• InChIKey: BAKQMOSGYGQJOJ-UPUXHGCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate
• IUPAC Traditional name: (2R,3S,4R,5R)-2,3-bis(acetyloxy)-6,8-dioxabicyclo[3.2.1]octan-4-yl acetate
• Synonyms: 2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-glucopyranose; Triacetyllevoglucosan; NSC 25284; 1,6-Anhydro-β-D-glucopyranose 2,3,4-Triacetate

Database IDs

• CAS Number: 13242-55-2
• PubChem SID: 162254810
• PubChem CID: 71313422

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.44745943
• LogD (pH = 7.4): -0.44745943
• Log P: -0.44745943
• Molar Refractivity: 59.8678 cm^3
• Polarizability: 25.374388 Å^3
• Polar Surface Area: 97.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 108-109°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A648200

1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, and macrolide antibiotics) as

REFERENCES

• Fraser-Reid, B., et al. J. Am. Chem. Soc. 106, 731 (1984)
• Edwards, M.P., et al. J. Org. Chem. 49, 3503 (1984)
• Kelly, A.G., and Roberts, J.S. J. Chem. Soc., Chem. Commun. 228, (1984)
• Ogawa, T., et al. Carbohydr. Res. 57, C31 (1984)
• Isobe, M., et al. Te