7-{[(2S,3R,4S,5R,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-4-methyl-2H-chromen-2-one

• ChemBase ID: 174499
• Molecular Formular: C32H36O8Si
• Molecular Mass: 576.70894
• Monoisotopic Mass: 576.21794464
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)Oc1ccc2c(c1)oc(=O)cc2C)O)O)O
• Canonical SMILES: O=c1cc(C)c2c(o1)cc(cc2)O[C@@H]1O[C@@H](CO[Si](C(C)(C)C)(c2ccccc2)c2ccccc2)[C@@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C32H36O8Si/c1-20-17-27(33)39-25-18-21(15-16-24(20)25)38-31-30(36)29(35)28(34)26(40-31)19-37-41(32(2,3)4,22-11-7-5-8-12-22)23-13-9-6-10-14-23/h5-18,26,28-31,34-36H,19H2,1-4H3/t26-,28+,29+,30-,31-/m1/s1
• InChIKey: YTHDSJIOVBDTQV-HPLFBIAMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-{[(2S,3R,4S,5R,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-4-methyl-2H-chromen-2-one
• IUPAC Traditional name: 7-{[(2S,3R,4S,5R,6R)-6-{[(tert-butyldiphenylsilyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-4-methylchromen-2-one
• Synonyms: 7-[[6-O-[(1,1-Dimethylethyl)diphenylsilyl]-β-D-galactopyranosyl]oxy]-4-methyl-2H-1-benzopyran-2-one; 4-Methylumbelliferyl 6-O-(tert-Butyldiphenylsilyl)-β-D-galactopyranoside

Database IDs

• CAS Number: 296776-03-9
• PubChem SID: 164230409
• PubChem CID: 71750680

CALCULATED PROPERTIES

• Acid pKa: 12.202126
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 4.9074
• LogD (pH = 7.4): 4.907393
• Log P: 4.9074
• Molar Refractivity: 149.1924 cm^3
• Polarizability: 61.27559 Å^3
• Polar Surface Area: 114.68 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - M334355

Intermediate in the production of fluorescent indicators, used to determine Sulphatase activity.

REFERENCES

• Simpson, H., et al.: J. Biomed. Sci., 50, 164 (1993)
• Harrison, J., et al.: Bioorg. Med. Chem. Lett., 11, 141 (1993)
• Newstead, S., et al.: Biochem., 44, 9117 (1993)