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

• ChemBase ID: 160659
• Molecular Formular: C20H22O9S2
• Molecular Mass: 470.51328
• Monoisotopic Mass: 470.07052428
• SMILES: [C@H]12[C@@H](C([C@@H]([C@H](CO1)O2)OS(=O)(=O)c1ccc(cc1)C)O)OS(=O)(=O)c1ccc(cc1)C
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)O[C@H]1[C@H]2OC[C@H](O2)[C@H](C1O)OS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C20H22O9S2/c1-12-3-7-14(8-4-12)30(22,23)28-18-16-11-26-20(27-16)19(17(18)21)29-31(24,25)15-9-5-13(2)6-10-15/h3-10,16-21H,11H2,1-2H3/t16-,17?,18-,19-,20-/m1/s1
• InChIKey: NJSSICCENMLTKO-HRCBOCMUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,4R,5R)-3-hydroxy-2-[(4-methylbenzenesulfonyl)oxy]-6,8-dioxabicyclo[3.2.1]octan-4-yl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: (1R,2S,4R,5R)-3-hydroxy-2-[(4-methylbenzenesulfonyl)oxy]-6,8-dioxabicyclo[3.2.1]octan-4-yl 4-methylbenzenesulfonate
• Synonyms: 1,6-Anhydro-β-D-glucopyranose 2,4-Bis(4-methylbenzenesulfonate); Levoglucosan 2,4-Di-p-toluenesulfonate; 1,6-Anhydro-2,4-di-O-p-toluenesulfonyl-β-D-glucopyranose

Database IDs

• CAS Number: 20204-80-2
• PubChem SID: 162254794
• PubChem CID: 46783444

CALCULATED PROPERTIES

• Acid pKa: 12.838256
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 3.3573878
• LogD (pH = 7.4): 3.357386
• Log P: 3.3573878
• Molar Refractivity: 108.2987 cm^3
• Polarizability: 44.876255 Å^3
• Polar Surface Area: 125.43 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Yellow Solid
• Melting Point: 108-110°C

DETAILS

Toronto Research Chemicals - A637865

A protected Levoglucosan, used in the syntheses with anhydro sugars.

REFERENCES

• Delorme, D., et al.: J. Med. Chem., 39, 3951 (1996)