(1S,2S,7S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.03,7]dodecane-2,8-diol

• ChemBase ID: 167758
• Molecular Formular: C12H20O6
• Molecular Mass: 260.2836
• Monoisotopic Mass: 260.12598836
• SMILES: C12[C@@H](OC(O2)(C)C)[C@H](O)C2[C@H](C1O)OC(O2)(C)C
• Canonical SMILES: OC1C2OC(O[C@H]2[C@@H](C2[C@H]1OC(O2)(C)C)O)(C)C
• InChI: InChI=1S/C12H20O6/c1-11(2)15-7-5(13)9-10(6(14)8(7)16-11)18-12(3,4)17-9/h5-10,13-14H,1-4H3/t5-,6?,7+,8?,9?,10+/m1/s1
• InChIKey: LDPFQVWIUACVFE-MMOXHJAGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,7S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.0^3,^7]dodecane-2,8-diol
• IUPAC Traditional name: (1S,2S,7S)-5,5,11,11-tetramethyl-4,6,10,12-tetraoxatricyclo[7.3.0.0^3,^7]dodecane-2,8-diol
• Synonyms: 1,2:4,5-Bis-O-(1-methylethylidene)-myo-inositol; 1,2:4,5-Bis-O-(1-methylethylidene)-DL-myo-inositol; 1,2:4,5-Diisopropylidene D,L-myo-Inositol

Database IDs

• CAS Number: 98974-89-1
• PubChem SID: 162261891
• PubChem CID: 45039044

CALCULATED PROPERTIES

• Acid pKa: 12.729223
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.37716046
• LogD (pH = 7.4): -0.37716246
• Log P: -0.37716043
• Molar Refractivity: 60.189 cm^3
• Polarizability: 24.810371 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMSO; Methanol
• Apperance: White Solid
• Melting Point: 159-162°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D458775

1,2:4,5-Diisopropylidene D,L-myo-Inositol is used in the synthesis of (±)-3-O-alkylated myo-inositol 1,4,5-trisphosphate analogs as potent receptor ligands and enzyme inhibitors.

REFERENCES

• Leigh, A., et al.: Biochemistry, 31, 8978 (1992)
• Bruzik, K., et al.: Bioorg. Med. Chem., 2, 49 (1992)
• Ryan, M., et al.: J. Med. Chem., 39, 4366 (1992)