(4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-[(tert-butyldimethylsilyl)oxy]oxan-2-one

• ChemBase ID: 172418
• Molecular Formular: C25H42O4Si
• Molecular Mass: 434.68408
• Monoisotopic Mass: 434.28523636
• SMILES: C1[C@H](C=C2[C@H]([C@H]1O)[C@H]([C@H](C=C2)C)CC[C@@H]1C[C@H](CC(=O)O1)O[Si](C(C)(C)C)(C)C)C
• Canonical SMILES: O=C1C[C@@H](C[C@H](O1)CC[C@H]1[C@@H](C)C=CC2=C[C@@H](C[C@@H]([C@H]12)O)C)O[Si](C(C)(C)C)(C)C
• InChI: InChI=1S/C25H42O4Si/c1-16-12-18-9-8-17(2)21(24(18)22(26)13-16)11-10-19-14-20(15-23(27)28-19)29-30(6,7)25(3,4)5/h8-9,12,16-17,19-22,24,26H,10-11,13-15H2,1-7H3/t16-,17-,19+,20+,21-,22-,24-/m0/s1
• InChIKey: MJLUKJALEPACMG-RVTXAWHXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-[(tert-butyldimethylsilyl)oxy]oxan-2-one
• IUPAC Traditional name: (4R,6R)-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}-4-[(tert-butyldimethylsilyl)oxy]oxan-2-one
• Synonyms: (4R,6R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl]ethyl]tetrahydro-2H-pyran-2-one; Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether

Database IDs

• CAS Number: 79902-31-1
• PubChem SID: 164228328
• PubChem CID: 10961059

CALCULATED PROPERTIES

• Acid pKa: 19.795877
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.315
• LogD (pH = 7.4): 4.315
• Log P: 4.315
• Molar Refractivity: 120.0766 cm^3
• Polarizability: 49.11228 Å^3
• Polar Surface Area: 55.76 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; DMF; DMSO; Ether; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - L472240

An intermediate used for synthesis of Simvastatin precursor (H941625).

REFERENCES

• Hoffman, W., et al.: J. Med. Chem., 29, 849 (1986)
• Jacobsen, W., et al.: Drug Metab. Dispos., 27, 173 (1986)
• Igel, M., et al.: Eur. J. Clin. Pharmacol., 57, 357 (1986)