(4S,5S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxane-2,3,4,5-tetrol

• ChemBase ID: 163347
• Molecular Formular: C12H26O6Si
• Molecular Mass: 294.41674
• Monoisotopic Mass: 294.14986508
• SMILES: [C@@H]1([C@@H](C(C(OC1CO[Si](C(C)(C)C)(C)C)O)O)O)O
• Canonical SMILES: OC1OC(CO[Si](C(C)(C)C)(C)C)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C12H26O6Si/c1-12(2,3)19(4,5)17-6-7-8(13)9(14)10(15)11(16)18-7/h7-11,13-16H,6H2,1-5H3/t7?,8-,9+,10?,11?/m1/s1
• InChIKey: AIJBYEYYSZEZMQ-SQQPQDOJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxane-2,3,4,5-tetrol
• IUPAC Traditional name: (4S,5S)-6-{[(tert-butyldimethylsilyl)oxy]methyl}oxane-2,3,4,5-tetrol
• Synonyms: 6-O-(tert-Butyldimethylsilyl)-D-Glucopyranose; 6-O-(tert-Butyldimethylsilyl)-Glucopyranose; 6-O-(tert-Butyldimethylsilyl)-D-glucose

Database IDs

• PubChem SID: 162257482
• PubChem CID: 71314406

CALCULATED PROPERTIES

• Acid pKa: 11.298363
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.3968007
• LogD (pH = 7.4): -0.39685482
• Log P: -0.3968
• Molar Refractivity: 65.7715 cm^3
• Polarizability: 29.02798 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Methanol
• Apperance: White Solid

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B691305

D-Glucose derivative. Used in enzymic synthesis of cyclohexyl-α and β-D-glucosides.

REFERENCES

• Wang, R., et al.: J. Mol. Catal. B. Enz., 56, 131 (2009)