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

Base Information

• Chemical Name: 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
• CAS No.: 79902-31-1
• Molecular Formula: C25H42 O4 Si
• Molecular Weight: 434.692
• DSSTox Substance ID: DTXSID10449885
• Nikkaji Number: J2.943.382H
• Mol file: 79902-31-1.mol

Synonyms:79902-31-1;(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)-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;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;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;SCHEMBL8013814;DTXSID10449885;MJLUKJALEPACMG-RVTXAWHXSA-N;AC-768;AKOS025402287;ES-2538;Lovastatin Diol Lactone 4-tert-Butyldimethyl Ether;(4R,6R)-4-(tert-Butyldimethylsiloxy)-6-[2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalene-1-yl]ethyl]-3,4,5,6-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

Chemical Property of 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

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.514
• Boiling Point: 540.396°C at 760 mmHg
• Flash Point: 280.622°C
• PSA: 55.76000
• Density: 1.047g/cm³
• LogP: 5.62800
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform, Methanol (Sparingly, Heated)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 434.28523635
• Heavy Atom Count: 30
• Complexity: 690

Purity/Quality:

98%min ^*data from raw suppliers

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 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C2C(C(C=CC2=C1)C)CCC3CC(CC(=O)O3)O[Si](C)(C)C(C)(C)C)O
• Isomeric SMILES: C[C@@H]1C[C@@H]([C@@H]2[C@H]([C@H](C=CC2=C1)C)CC[C@@H]3C[C@H](CC(=O)O3)O[Si](C)(C)C(C)(C)C)O
• Uses: An intermediate used for synthesis of Simvastatin precursor (H941625).

Technology Process of 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

There total 6 articles about 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 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.4%

(4R,6R)-4-hydroxy-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 (151006-15-4,79952-42-4,76343-78-7,81739-25-5) + tert-butyldimethylsilyl chloride (18162-48-6) → (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 (79902-31-1)

Guidance literature:

With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 60 ℃; for 3h;

Reference yield: 46.0%

acetaldehyde (75-07-0,9002-91-9) + 6(R)-<2-<8-<(trimethylsilyl)oxy>-2(S),6(S)-dimethyl-1,2,6,8a(R)-tetrahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyranone (143746-93-4) → (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 (79902-31-1) + 6(R)-<2-<8-oxo-2(S),6(S)-dimethyl-7(S)-<1(S)-hydroxyethyl>-1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one (136432-18-3) + (4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-{2-[(1S,2S,6S,7S,8aR)-7-((R)-1-hydroxy-ethyl)-2,6-dimethyl-8-oxo-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-ethyl}-tetrahydro-pyran-2-one (136521-50-1)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 - -50 ℃; for 2h;

DOI:10.1021/jm00099a009

Reference yield:

lovastatin (75330-75-5,79952-44-6) → (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 (79902-31-1)

Guidance literature:

Multi-step reaction with 3 steps

1: aq. LiOH / Heating

2: 140 mg / toluene / 1 h / Heating

3: 74 percent / imidazole / dimethylformamide / 18 h / 20 °C

With 1H-imidazole; lithium hydroxide; In N,N-dimethyl-formamide; toluene;

DOI:10.1039/b207721c

upstream raw materials:

acetaldehyde

6(R)-<2-<8-<(trimethylsilyl)oxy>-2(S),6(S)-dimethyl-1,2,6,8a(R)-tetrahydronaphthyl-1(S)>ethyl>-4(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyranone

(4R,6R)-4-hydroxy-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

tert-butyldimethylsilyl chloride

Downstream raw materials:

<1S-<1α,3α,7β,8β(2S^*,4S^*)8aβ>>-8-<2-<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 benzeneacetate

6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one

6(R)-[2-[8(S)-(2-trifluoromethyl-benzoyloxy)-2(S),6(R) dimethyl 1,2,6,7,8,8a(R)-hexahydronaphthyl-1(S)]ethyl]-4(R)-tert-butyl-dimethylsilyloxy-3,4,5,6-tetrahydro-2H-pyran-2-one

(1S,3R,7S,8S,8αR)-8-(2-((2R,4R)-4-((tert-butyldimethylchlorosilane)oxy)-6-oxohexahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8α-hexahydronaphthalene-1-yl(4-nitrophenyl)carbonate

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