(3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyl)oxy]-6-(hydroxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyran-6-ol

• ChemBase ID: 163410
• Molecular Formular: C25H34O6Si
• Molecular Mass: 458.61936
• Monoisotopic Mass: 458.21246534
• SMILES: O1C[C@@H]2[C@H]([C@@H]([C@@]1(O)CO)O[Si](c1ccccc1)(c1ccccc1)C(C)(C)C)OC(O2)(C)C
• Canonical SMILES: OC[C@@]1(O)OC[C@@H]2[C@H]([C@@H]1O[Si](C(C)(C)C)(c1ccccc1)c1ccccc1)OC(O2)(C)C
• InChI: InChI=1S/C25H34O6Si/c1-23(2,3)32(18-12-8-6-9-13-18,19-14-10-7-11-15-19)31-22-21-20(29-24(4,5)30-21)16-28-25(22,27)17-26/h6-15,20-22,26-27H,16-17H2,1-5H3/t20-,21-,22+,25-/m1/s1
• InChIKey: LYEYVIPMFIHSLX-ILSIFQBBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyl)oxy]-6-(hydroxymethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-c]pyran-6-ol
• IUPAC Traditional name: (3aR,6R,7S,7aR)-7-[(tert-butyldiphenylsilyl)oxy]-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ol
• Synonyms: 3-tert-Butyldiphenylsilyl-4,5-O-(1-methylethyldiene)-β-D-fructopyranose

Database IDs

• PubChem SID: 162257545
• PubChem CID: 57370062

CALCULATED PROPERTIES

• Acid pKa: 10.316833
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 5.243593
• LogD (pH = 7.4): 5.243075
• Log P: 5.2436
• Molar Refractivity: 117.8043 cm^3
• Polarizability: 49.351864 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Yellow Syrup

DETAILS

Toronto Research Chemicals - B691715

Intermediate in the preparation of 2,3-Desisopropylidene Topiramate, a metabolite of Topiramate