[(3aS,5S,6R,6aS)-6-hydroxy-2,2-dimethyl-5-{[(4-methylbenzenesulfonyl)oxy]methyl}-tetrahydro-2H-furo[2,3-d][1,3]dioxol-3a-yl]methyl 4-methylbenzene-1-sulfonate

• ChemBase ID: 171882
• Molecular Formular: C23H28O10S2
• Molecular Mass: 528.59242
• Monoisotopic Mass: 528.1123891
• SMILES: [C@@H]1(O)[C@H](COS(=O)(=O)c2ccc(cc2)C)O[C@@]2(COS(=O)(=O)c3ccc(cc3)C)OC(O[C@H]12)(C)C
• Canonical SMILES: Cc1ccc(cc1)S(=O)(=O)OC[C@@H]1O[C@@]2([C@@H]([C@@H]1O)OC(O2)(C)C)COS(=O)(=O)c1ccc(cc1)C
• InChI: InChI=1S/C23H28O10S2/c1-15-5-9-17(10-6-15)34(25,26)29-13-19-20(24)21-23(31-19,33-22(3,4)32-21)14-30-35(27,28)18-11-7-16(2)8-12-18/h5-12,19-21,24H,13-14H2,1-4H3/t19-,20+,21-,23-/m0/s1
• InChIKey: RWMGKKKBAWACGX-KGSLCBSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3aS,5S,6R,6aS)-6-hydroxy-2,2-dimethyl-5-{[(4-methylbenzenesulfonyl)oxy]methyl}-tetrahydro-2H-furo[2,3-d][1,3]dioxol-3a-yl]methyl 4-methylbenzene-1-sulfonate
• IUPAC Traditional name: [(3aS,5S,6R,6aS)-6-hydroxy-2,2-dimethyl-5-{[(4-methylbenzenesulfonyl)oxy]methyl}-dihydro-5H-furo[2,3-d][1,3]dioxol-3a-yl]methyl 4-methylbenzenesulfonate
• Synonyms: 2,3-O-(1-Methylethylidene)-α-L-sorbofuranose 1,6-Bis(4-methylbenzene-sulfonate); 2,3-O-Isopropylidene 1,6-Di-p-toluenesulfonate α-L-Sorbofuranose; 2,3-O-Isopropylidene-1,6-ditosyl-L-sorboseSee D494335

Database IDs

• CAS Number: 2484-55-1
• PubChem SID: 164227792
• PubChem CID: 71749601

CALCULATED PROPERTIES

• Acid pKa: 12.951753
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 4.0726485
• LogD (pH = 7.4): 4.0726476
• Log P: 4.0726485
• Molar Refractivity: 124.4532 cm^3
• Polarizability: 51.094276 Å^3
• Polar Surface Area: 134.66 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Solid
• Melting Point: 118-120°C

DETAILS

Toronto Research Chemicals - I824925

Used in the synthesis of oxy-bridged bicyclic aza-sugar and thio-sugar as potential glycosidase inhibitors.

REFERENCES

• Hoffman, D., et al.: Biochemistry, 7, 4479 (1968)
• Yoshikawa, M., et al.: Bioorg. Med. Chem., 10, 1547 (1968)