(1R,2S,3S,4R,5R)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl 4-methylbenzene-1-sulfonate

• ChemBase ID: 160697
• Molecular Formular: C13H16O7S
• Molecular Mass: 316.32694
• Monoisotopic Mass: 316.06167385
• SMILES: [C@H]12[C@@H]([C@H]([C@@H]([C@H](CO1)O2)O)O)OS(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: O[C@@H]1[C@@H](OS(=O)(=O)c2ccc(cc2)C)[C@H]2OC[C@@H]([C@H]1O)O2
• InChI: InChI=1S/C13H16O7S/c1-7-2-4-8(5-3-7)21(16,17)20-12-11(15)10(14)9-6-18-13(12)19-9/h2-5,9-15H,6H2,1H3/t9-,10-,11+,12-,13-/m1/s1
• InChIKey: SLBPXGGBTQVDQH-UJPOAAIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,3S,4R,5R)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: (1R,2S,3S,4R,5R)-2,3-dihydroxy-6,8-dioxabicyclo[3.2.1]octan-4-yl 4-methylbenzenesulfonate
• Synonyms: 1,6-Anhydro-β-D-glucopyranose 2-(4-Methylbenzenesulfonate); Levoglucosan 2-p-Toluenesulfonate; 1,6-Anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose

Database IDs

• CAS Number: 3868-05-1
• PubChem SID: 162254832
• PubChem CID: 10543415

CALCULATED PROPERTIES

• Acid pKa: 12.676524
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.793276
• LogD (pH = 7.4): 0.79327375
• Log P: 0.7932761
• Molar Refractivity: 70.356 cm^3
• Polarizability: 29.323275 Å^3
• Polar Surface Area: 102.29 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 117-118°C

DETAILS

Toronto Research Chemicals - A658265

1,6-Anhydro-2-O-p-toluenesulfonyl-β-D-glucopyranose is used in the syntheses with anhydro sugars.

REFERENCES

• MacLeod, J.M., et al.: Carbohydr. Res., 30, 337 (1973)