(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one

Base Information

• Chemical Name: (E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one
• CAS No.: 864430-38-6
• Molecular Formula: C₃₆H₅₆O₂Si
• Molecular Weight: 548.925
• Mol file: 864430-38-6.mol

Synonyms:(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one

Chemical Property of (E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one

There total 2 articles about (E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-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: 75.0%

[4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-2-oxo-butyl]-phosphonic acid diethyl ester (851121-38-5) + myristylaldehyde (124-25-4,511542-15-7) → (E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one (864430-38-6)

Guidance literature:

[4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-2-oxo-butyl]-phosphonic acid diethyl ester; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃;

myristylaldehyde; In tetrahydrofuran; at -78 - 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.06.073

Reference yield:

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester (95514-03-7) → (E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one (864430-38-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran / -78 °C

1.2: 65 percent / tetrahydrofuran / 2 h / -78 °C

2.1: n-BuLi / tetrahydrofuran / -78 - 20 °C

2.2: 75 percent / tetrahydrofuran / 3 h / -78 - 20 °C

With n-butyllithium; In tetrahydrofuran; 2.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2005.06.073

Reference yield: 85.0%

(E)-(S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-one (864430-38-6) → (E)-(2S,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-ol (864430-39-7)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2005.06.073

upstream raw materials:

[4-(tert-butyl-diphenyl-silanyloxy)-1,3-dimethyl-2-oxo-butyl]-phosphonic acid diethyl ester

myristylaldehyde

(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

Downstream raw materials:

(E)-(2S,3S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadec-4-en-3-ol

(1S,2S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methyl-1-((2R,3R)-2-methyl-3-tridecyl-oxiranyl)-propan-1-ol

(2S,3S,4S,5R)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-octadecane-3,5-diol

(S)-3-Benzyloxy-2-((2S,3R)-3-benzyloxy-2-{(S)-3-methyl-2-[(R)-2-((4R,5S,6R)-2,2,5-trimethyl-6-tridecyl-[1,3]dioxan-4-yl)-propionylamino]-butyrylamino}-butyrylamino)-propionic acid methyl ester