<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

Base Information

• Chemical Name: <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
• CAS No.: 116996-45-3
• Molecular Formula: C₃₈H₅₄O₄Si
• Molecular Weight: 602.93
• Mol file: 116996-45-3.mol

Synonyms:<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

Chemical Property of <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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <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

There total 10 articles about <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 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: 82.0%

<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-1<<(1,1-Dimethyethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-3,5-heptanediol (148933-92-0) + acetone (67-64-1) → <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)

Guidance literature:

With toluene-4-sulfonic acid;

DOI:10.1039/c39930000647

Reference yield:

<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) → <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)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / (Ph₃P)3RhCl / toluene; acetonitrile / 2.5 h / Heating

2: 1.) LDA / 1.)Et₂O, -78 deg C, 45 min; 2.) -78 deg C, 10 min

3: 85 percent / i-Pr₂NH / DMAP / diethyl ether / 24 h / Ambient temperature

4: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> r.t., 3 h

5: 86 percent / C₈K, TiCl₃ / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h

6: 1.) Bu₄NF ; 2.) t-BuPh₂SiCl, Et₃N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH₂Cl₂, r.t., 24 h

With Wilkinson's catalyst; titanium(III) chloride; tetrabutyl ammonium fluoride; ozone; triethylamine; diisopropylamine; triphenylphosphine; tert-butylchlorodiphenylsilane; lithium diisopropyl amide; dmap; In 1,2-dimethoxyethane; diethyl ether; toluene; acetonitrile;

DOI:10.1021/ja00228a067

Reference yield:

<4S-<4α,5α(4S*,6R*),6β(1R*,3S*)>>-5-<2-<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-4-methyl-6-<3-methyl-1-<(triethylsilyl)oxy>-4-pentenyl>-2-cyclohexen-1-one (117020-89-0) → <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)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C -> r.t., 3 h

2: 86 percent / C₈K, TiCl₃ / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 4 h

3: 1.) Bu₄NF ; 2.) t-BuPh₂SiCl, Et₃N / 2.) DMAP / 1.) THF, r.t., 22 h; 2.) CH₂Cl₂, r.t., 24 h

With titanium(III) chloride; tetrabutyl ammonium fluoride; ozone; triethylamine; triphenylphosphine; tert-butylchlorodiphenylsilane; dmap; In 1,2-dimethoxyethane;

DOI:10.1021/ja00228a067

upstream raw materials:

<1S-<1α,3α,7β,8β(4Σ^*,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-naphthalenyl>oxy>triethylsilane

<1S-<1α(3R*,5S*),2α,6β,8β,8aα>>-1<<(1,1-Dimethyethyl)diphenylsilyl>oxy>-7-(1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthalenyl)-3,5-heptanediol

acetone

(1S,3R,7S,8S,8aR)-8-{2-[(4R,6S)-6-(2-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-ethyl}-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

Downstream raw materials:

(3R,7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3,7-dimethyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one

lovastatin

<1R-<1α,2α,4α,4aβ,5β(4R*,6S*),6β,7β>>-5-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-7-(dimethylphenylsilyl)-1,2,3,4,4a,5,6,7-octahydro-2,6-dimethyl-1,4-naphthalenediol