(3aR,4S,5R,6R,7S,7aS)-4,6,7-tris(acetyloxy)-hexahydrospiro[1,3-benzodioxole-2,1'-cyclohexane]-5-yl acetate

• ChemBase ID: 165210
• Molecular Formular: C20H28O10
• Molecular Mass: 428.43032
• Monoisotopic Mass: 428.1682471
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H]2[C@@H]([C@H]1OC(=O)C)OC1(O2)CCCCC1)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@@H]2OC3(O[C@@H]2[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)CCCCC3
• InChI: InChI=1S/C20H28O10/c1-10(21)25-14-15(26-11(2)22)17(28-13(4)24)19-18(16(14)27-12(3)23)29-20(30-19)8-6-5-7-9-20/h14-19H,5-9H2,1-4H3/t14-,15-,16+,17+,18-,19+/m0/s1
• InChIKey: FQPTWYQWMBTSMM-DTXAGUPXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3aR,4S,5R,6R,7S,7aS)-4,6,7-tris(acetyloxy)-hexahydrospiro[1,3-benzodioxole-2,1'-cyclohexane]-5-yl acetate
• IUPAC Traditional name: (3aR,4S,5R,6R,7S,7aS)-4,6,7-tris(acetyloxy)-hexahydrospiro[1,3-benzodioxole-2,1'-cyclohexane]-5-yl acetate
• Synonyms: 1,2-O-Cyclohexylidene-myo-inositol Tetraacetate; 2,3-O-cyclohexylidene-inositol Tetraacetate; 1,2-Cyclohexylidene Tetra-O-acetyl myo-Inositol

Database IDs

• CAS Number: 39110-61-7
• PubChem SID: 162259343
• PubChem CID: 29976586

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 0.93950564
• LogD (pH = 7.4): 0.93950564
• Log P: 0.93950564
• Molar Refractivity: 96.3244 cm^3
• Polarizability: 40.10504 Å^3
• Polar Surface Area: 123.66 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Crystalline Solid
• Melting Point: 104-108°C

DETAILS

Toronto Research Chemicals - C988045

1,2-O-Cyclohexylidene-myo-inositol Tetraacetate is used in the synthesis of inhibitors of cerebroside metabolism such as: N-Hexylglucosylsphingosine, Conduritol B epoxide, DL-2-Decanoylamino-3-morpholinopropiophenone, DL-2-Decanoylamino-3-morpholino-1-phe

REFERENCES

• Lee, K.J., et al.: Carbohydr. Res., 144, 148 (1985)