(1S,3R,7S,8S,8aR)-8-{2-[(2R,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(2H3)methylbutanoate

• ChemBase ID: 173442
• Molecular Formular: C30H50O5Si
• Molecular Mass: 518.8005
• Monoisotopic Mass: 518.34275123
• SMILES: [C@@H]1(C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H]1OC(=O)C[C@H](C1)O[Si](C(C)(C)C)(C)C)C)OC(=O)[C@@H](CC)C
• Canonical SMILES: CC[C@H](C(=O)O[C@H]1C[C@@H](C)C=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](CC(=O)O1)O[Si](C(C)(C)C)(C)C)[C@H](C=C2)C)C
• InChI: InChI=1S/C30H50O5Si/c1-10-20(3)29(32)34-26-16-19(2)15-22-12-11-21(4)25(28(22)26)14-13-23-17-24(18-27(31)33-23)35-36(8,9)30(5,6)7/h11-12,15,19-21,23-26,28H,10,13-14,16-18H2,1-9H3/t19-,20+,21-,23+,24-,25-,26-,28-/m0/s1
• InChIKey: YZUJIMXHROAZNZ-SFVYKUKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• IUPAC Traditional name: (1S,3R,7S,8S,8aR)-8-{2-[(2R,4S)-4-[(tert-butyldimethylsilyl)oxy]-6-oxooxan-2-yl]ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-(^2H₃)methylbutanoate
• Synonyms: (2S)-2-Methylbutanoic Acid (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]tetrahydro-6-oxo-2H-pyran-2-yl]ethyl]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl Ester; 6(R)-{2-[8(S)-2-Methyl-d3-butyryloxy-2(S),6(R)-dimethyl-1,2,6,7,8,8d(R)-hexahydro-1(S)-naphthyl]ethyl}-4(R)-tert-butyldimethylsilyloxy-3,4,5,6-tetrahydro-2H-pyran-2-one

Database IDs

• PubChem SID: 164229352
• PubChem CID: 71750249

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 6.331
• LogD (pH = 7.4): 6.331
• Log P: 6.331
• Molar Refractivity: 143.0305 cm^3
• Polarizability: 58.466503 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Foam

DETAILS

Toronto Research Chemicals - M294437

An intermediate in the synthesis of labelled Lovastatin an antihypercholesterolemic agent. A fungal metabolite, which is a potent inhibitor of HMG-CoA reductase.

REFERENCES

• Bilheimer, D.W., et al.: Proc. Nat. Acad. Sci. USA, 80, 4124 (1983)