(2S,4S,5S)-2-{[(2S,3R,5R)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 163964
• Molecular Formular: C12H20O10
• Molecular Mass: 324.2812
• Monoisotopic Mass: 324.10564684
• SMILES: [C@@H]1([C@@H](C([C@@H](OC1CO)O[C@H]1[C@@H](C([C@@H]2OC1CO2)O)O)O)O)O
• Canonical SMILES: OCC1O[C@@H](O[C@@H]2C3CO[C@@H](O3)C([C@H]2O)O)C([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C12H20O10/c13-1-3-5(14)6(15)8(17)12(20-3)22-10-4-2-19-11(21-4)9(18)7(10)16/h3-18H,1-2H2/t3?,4?,5-,6+,7-,8?,9?,10-,11-,12+/m1/s1
• InChIKey: LTYZUJSCZCPGHH-KDQNYLTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-2-{[(2S,3R,5R)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2S,4S,5S)-2-{[(2S,3R,5R)-3,4-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: 1,6-Anhydro-4-O-β-D-glucopyranosyl-β-D-glucopyranose; 1,6-Anhydro-β-cellobiose; Cellobiosan

Database IDs

• CAS Number: 35405-71-1
• PubChem SID: 162258099
• PubChem CID: 46780206

CALCULATED PROPERTIES

• Acid pKa: 11.940894
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -3.5416715
• LogD (pH = 7.4): -3.5416837
• Log P: -3.5416713
• Molar Refractivity: 64.8266 cm^3
• Polarizability: 27.628908 Å^3
• Polar Surface Area: 158.3 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C254950

A common anhydro sugar in wood pyrolysis oils.

REFERENCES

• Fraser, M., et al.: Environ. Sci. Technol., 34, 4560 (2000)
• Mosier, N., et al.: Biotechnol. Bioeng., 79, 610 (2000)
• Bridgwater, T., et al.: J. Sci. Food Agric., 86, 1755 (2000)