trimethyl({[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis[(trimethylsilyl)oxy]oxan-2-yl]methoxy})silane

• ChemBase ID: 176326
• Molecular Formular: C21H52O6Si5
• Molecular Mass: 541.06148
• Monoisotopic Mass: 540.26102204
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C
• Canonical SMILES: C[Si](O[C@H]1O[C@@H](CO[Si](C)(C)C)[C@@H]([C@@H]([C@@H]1O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)(C)C
• InChI: InChI=1S/C21H52O6Si5/c1-28(2,3)22-16-17-18(24-29(4,5)6)19(25-30(7,8)9)20(26-31(10,11)12)21(23-17)27-32(13,14)15/h17-21H,16H2,1-15H3/t17-,18+,19+,20-,21-/m1/s1
• InChIKey: PPFHNIVPOLWPCF-XDWAVFMPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethyl({[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis[(trimethylsilyl)oxy]oxan-2-yl]methoxy})silane
• IUPAC Traditional name: trimethyl({[(2R,3S,4S,5R,6R)-3,4,5,6-tetrakis[(trimethylsilyl)oxy]oxan-2-yl]methoxy})silane
• Synonyms: 1,2,3,4,6-Pentakis-O-(trimethylsilyl)-α-D-galactopyranose; 1,2,3,4,6-Pentakis-O-(trimethylsilyl) α-D-Galactose

Database IDs

• CAS Number: 32166-80-6
• PubChem SID: 164232236
• PubChem CID: 6427851

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 7.4162
• LogD (pH = 7.4): 7.4162
• Log P: 7.4162
• Molar Refractivity: 116.5529 cm^3
• Polarizability: 57.548737 Å^3
• Polar Surface Area: 55.38 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Colorless Oil

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - P274125

1,2,3,4,6-Pentakis-O-(trimethylsilyl) α-D-Galactose is used in the synthesis of truncated analogues of the iNKT cell agonist, α-galactosyl ceramide (KRN7000).

REFERENCES

• Hong, S., et al.: Immunol. Rev., 169, 31 (1999)
• Crowe, N., et al.: J. Immunol., 171, 4020 (1999)
• Forestier, C., et al.: J. Immunol., 178, 1415 (1999)