<4R-<4α(4R^*,5R^*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

Base Information

• Chemical Name: <4R-<4α(4R^*,5R^*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one
• CAS No.: 116996-32-8
• Molecular Formula: C₃₃H₄₆O₄Si
• Molecular Weight: 534.811

Synonyms:<4R-<4α(4R^*,5R^*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

Chemical Property of <4R-<4α(4R^*,5R^*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <4R-<4α(4R^*,5R^*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one

There total 39 articles about <4R-<4α(4R^*,5R^*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-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: 84.0%

1-Methoxy-2-methyl-3-oxopropyl <1R-<1α,5β,6β(4R*,6S*)>>-6-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-5-methyl-2-oxo-3-cyclohexene-1-carboxylate → <4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one (116996-32-8)

Guidance literature:

With hydrogen cation; In 1,4-dioxane; for 10h; Heating;

DOI:10.1021/jo00110a051

Reference yield: 50.0%

<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal (116996-31-7,126060-10-4) → <4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one (116996-32-8)

Guidance literature:

With Wilkinson's catalyst; In benzonitrile; toluene; for 2.5h; Heating;

DOI:10.1021/ja00164a024

Reference yield:

<1S-<1α,3α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol (116996-45-3) → <4R-<4α(4R*,5R*),6α>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-2-cyclohexen-1-one (116996-32-8)

Guidance literature:

Multi-step reaction with 12 steps

1: 82 percent / NaHCO₃, t-BuOOH, VO(acac)2 / benzene / 5 h / Ambient temperature

2: 1.) Li, CuCN / 1.) THF, 2.) THF, 5 h

3: 84 percent / NaHCO₃, t-BuOOH, VO(acac)2 / benzene / 3 h / Ambient temperature

4: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 0.33 h / 0 °C

5: 77 percent / PCC, NaOAc, 4 Angstroem molecular sieves / CH₂Cl₂ / 22.5 h

6: 100 percent / LDA, Et₃N / tetrahydrofuran; hexane / 1.) -78 deg C, 30 min, 2.) -78 deg C, 1 h; -78 deg C to r.t., 40 min

7: 92 percent / m-CPBA, NaHCO₃ / ethyl acetate / 1.5 h / 0 °C

8: 85 percent / Bu₄NF, AcOH / tetrahydrofuran / 5 h

9: PPTS / ethanol / 12 h

10: PPTS / 5 h

11: 66 percent / Pb(OAc)4 / benzene / 1 h / Ambient temperature

12: 84 percent / H(+) / dioxane / 10 h / Heating

With lead(IV) acetate; tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; 4 A molecular sieve; tetrabutyl ammonium fluoride; sodium acetate; pyridinium p-toluenesulfonate; hydrogen cation; lithium; sodium hydrogencarbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; ethyl acetate; benzene;

DOI:10.1021/jo00110a051

upstream raw materials:

<4R-<4α*(1R^*,2S^*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal

acetone

mevastatin

<1S-<1α,3α,7β,8β(4S^*,6R^*),8aβ>>-8-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenol

Downstream raw materials:

(4S,5S,6S)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-(1-hydroxy-pent-4-enyl)-4-methyl-cyclohex-2-enone

<4S-<4α,5α(4S^*,4S^*),6β(1R^*,3S^*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-6-(1-hydroxy-3-methyl-4-pentenyl)-4-methyl-2-cyclohexen-1-one

<4S(4α,5α,6β)>-5-(2-<(4S*,6R*)-6-<2-(t-butyldiphenylsilyloxy)ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl)-6-<(1R*,3S*)-3-ethyl-1-hydroxypent-4-enyl>-4-methylcyclohex-2-enone

lovastatin

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