Cas no 79902-31-1 (Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether)

Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether is a chemically modified derivative of lovastatin, featuring a tert-butyldimethylsilyl (TBDMS) ether group at the 4-position. This modification enhances the compound's stability and solubility, making it a valuable intermediate in synthetic organic chemistry, particularly for the preparation of statin analogs. The TBDMS protecting group allows selective functionalization of the molecule while safeguarding reactive hydroxyl groups during multi-step syntheses. Its structural features facilitate controlled derivatization, enabling researchers to explore structure-activity relationships in drug development. The compound is commonly utilized in pharmaceutical research for its role in producing high-purity intermediates with defined stereochemistry.
Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether structure
79902-31-1 structure
Product Name:Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether
CAS No:79902-31-1
MF:C25H42O4Si
MW:434.684089183807
CID:556772
PubChem ID:10961059
Update Time:2025-05-28

Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether Chemical and Physical Properties

Names and Identifiers

    • 2H-Pyran-2-one,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-,(4R,6R)-
    • Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether
    • (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-butyl(dimethyl)silyl]oxyoxan-2-one
    • 2H-Pyran-2-one,4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-...
    • 2H-Pyran-2-one,4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[2-[(1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethy
    • 4-(TERT-BUTYL-DIMETHYL-SILANYLOXY)-6-[2-(8-HYDROXY-2,6-DIMETHYL-1,2,6,7,8,8A-HEXAHYDRO NAPHTHALEN-1-YL)-ETHYL]-TETRAHYD...
    • Lovastatin Diol Lact
    • (4R,6R)-4-(tert-butyldimethylsilyloxy)-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-on
    • (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one
    • 1,7-Dioxaspiro[4.4]nonane-2,6-dione,8-(1,2-dihydroxyethyl)-9-hydroxy-4-(p-hydroxyphenyl)
    • Leucodrin
    • 6(R)-[2-(8(S)-Hydroxy]-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl]ethyl-4(R)-(t-butyl-dimethylsilyl)oxy-3,4,5,6-tetrahydro-2H-pyran-2-one
    • Lovastatin Diol Lactone 4-tert-Butyldimethyl Ether
    • 4-(tert-butyl-dimethyl-silanyloxy)-6-[2-(8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydro naphthalen-1-yl)-ethyl]-tetrahydro-pyran-2-one
    • AC-768
    • (4R,6R)-4-((tert-Butyldimethylsilyl)oxy)-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one
    • (4R,6R)-4-{[tert-Butyl(dimethyl)silyl]oxy}-6-{2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl}oxan-2-one
    • SCHEMBL8013814
    • DTXSID10449885
    • 79902-31-1
    • ES-2538
    • AKOS025402287
    • 4-(tert-Butyldimethylsilanyloxy)-6-[2-(8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl]tetrahydropyran-2-one
    • (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 (ACI)
    • 2H-Pyran-2-one, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[2-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)ethyl]tetrahydro-, [1S-[1α(4S*,6S*),2α,6β,8β,8aα]]- (ZCI)
    • (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;
    • 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
    • InChI Key： MJLUKJALEPACMG-RVTXAWHXSA-N
    • SMILES： C([C@H]1[C@@H](C)C=CC2=C[C@@H](C[C@@H]([C@H]12)O)C)C[C@H]1OC(=O)C[C@H](O[Si](C)(C)C(C)(C)C)C1

Computed Properties

  • Exact Mass: 434.28500
  • Monoisotopic Mass: 434.28523635g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 6
  • Complexity: 690
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 7
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 55.8?2

Experimental Properties

  • Density: 1.04±0.1 g/cm3 (20 oC 760 Torr),
  • Melting Point: 142-144 oC
  • Boiling Point: 540.396°C at 760 mmHg
  • Flash Point: 280.622°C
  • Refractive Index: 1.514
  • Solubility: Insuluble (2.7E-3 g/L) (25 oC),
  • PSA: 55.76000
  • LogP: 5.62800

Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether Pricemore >>

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Lovastatin Diol Lactone 4-tert-Butyldimethylsilyl Ether Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Lithium hydroxide Solvents: Methanol
1.2 Reagents: Imidazole Solvents: Dimethylformamide
Reference
Synthesis of (+)-dihydromevinolin by selective reduction of mevinolin
DeCamp, A. E.; et al, Journal of Organic Chemistry, 1989, 54(13), 3207-8

Production Method 2

Reaction Conditions
1.1 Solvents: Toluene ;  3 h, reflux
2.1 Reagents: Imidazole Solvents: Dimethylformamide ;  20 h, rt
Reference
Synthesis of deuterium-labeled simvastatin
Tian, Lei; et al, Journal of Labelled Compounds and Radiopharmaceuticals, 2011, 54(9), 625-628

Production Method 3

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  8 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  Water ;  4.5 h, pH 2, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized
1.4 Reagents: Imidazole Solvents: Dichloromethane ;  5.5 h, rt
Reference
Design and Synthesis of Dual-Action Inhibitors Targeting Histone Deacetylases and 3-Hydroxy-3-methylglutaryl Coenzyme A Reductase for Cancer Treatment
Chen, Jhih-Bin; et al, Journal of Medicinal Chemistry, 2013, 56(9), 3645-3655

Production Method 4

Reaction Conditions
1.1 Reagents: Potassium hydroxide Solvents: Methanol ,  Water ;  12 h, reflux
1.2 Reagents: Hydrochloric acid Solvents: Dichloromethane ,  Water ;  pH 2; 6 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water ;  neutralized
2.1 Reagents: Imidazole Solvents: Dichloromethane ;  6 h, rt
Reference
Discovery of an orally active VHL-recruiting PROTAC that achieves robust HMGCR degradation and potent hypolipidemic activity in-vivo
Luo, Guoshun; et al, Acta Pharmaceutica Sinica B, 2021, 11(5), 1300-1314

Production Method 5

Reaction Conditions
1.1 Solvents: Ethanol ,  Water ;  10 d, pH 6.5, 30 °C
2.1 Reagents: Lithium hydroxide Solvents: Water ;  overnight, reflux; reflux → rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  < pH 2, rt
2.3 Reagents: Calcium hydride Solvents: Toluene ;  1 h, reflux
3.1 Reagents: Imidazole Solvents: Dimethylformamide ;  18 h, rt
Reference
Transformations of cyclic nonaketides by Aspergillus terreus mutants blocked for lovastatin biosynthesis at the lovA and lovC genes
Sorensen, John L.; et al, Organic & Biomolecular Chemistry, 2003, 1(1), 50-59

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