<1S-<1α(R^*),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-naphthalenyl 2-methylbutanoate

Base Information

• Chemical Name: <1S-<1α(R^*),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-naphthalenyl 2-methylbutanoate
• CAS No.: 116996-46-4
• Molecular Formula: C₄₃H₆₂O₅Si
• Molecular Weight: 687.048
• Mol file: 116996-46-4.mol

Synonyms:<1S-<1α(R^*),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-naphthalenyl 2-methylbutanoate

Chemical Property of <1S-<1α(R^*),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-naphthalenyl 2-methylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1S-<1α(R^*),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-naphthalenyl 2-methylbutanoate

There total 10 articles about <1S-<1α(R^*),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-naphthalenyl 2-methylbutanoate 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: 97.0%

<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) + (S)-2-methylbutyric anhydride (84131-91-9) → <1S-<1α(R*),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-naphthalenyl 2-methylbutanoate (116996-46-4)

Guidance literature:

With triethylamine; dmap; In dichloromethane; for 88h; Ambient temperature;

DOI:10.1021/ja00228a067

Reference yield: 91.0%

<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) + (S)-(+)-2-methylbutyric anhydride (84131-91-9) → <1S-<1α(R*),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-naphthalenyl 2-methylbutanoate (116996-46-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 72h; Ambient temperature;

DOI:10.1021/ja00164a024

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(R*),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-naphthalenyl 2-methylbutanoate (116996-46-4)

Guidance literature:

Multi-step reaction with 7 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

7: 97 percent / Et₃N / DMAP / CH₂Cl₂ / 88 h / Ambient temperature

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; dichloromethane; toluene; acetonitrile;

DOI:10.1021/ja00228a067

upstream raw materials:

<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

(S)-(+)-2-methylbutyric anhydride

(S)-2-methylbutyric anhydride

<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

Downstream raw materials:

lovastatin