(-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester

Base Information

• Chemical Name: (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester
• CAS No.: 948859-73-2
• Molecular Formula: C₂₅H₃₄O₂SSi
• Molecular Weight: 426.695
• Mol file: 948859-73-2.mol

Synonyms:(-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester

Chemical Property of (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester

There total 7 articles about (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester 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:

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9) → (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester (948859-73-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

1.2: 95 percent / diethyl ether; various solvent(s) / 17 h / -75 °C

2.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

3.1: 1.491 g / CH₂Cl₂ / 24 h / Heating

With triethylsilane; palladium on activated charcoal; In diethyl ether; dichloromethane; 3.1: Wittig reaction;

DOI:10.1021/ol071078o

Reference yield:

(-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester (948859-72-1) → (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester (948859-73-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

2: 1.491 g / CH₂Cl₂ / 24 h / Heating

With triethylsilane; palladium on activated charcoal; In dichloromethane; 2: Wittig reaction;

DOI:10.1021/ol071078o

Reference yield:

(tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) → (-)-(E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hex-2-enethioic acid S-ethyl ester (948859-73-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 80 percent / CH₂Cl₂ / 24 h / Heating

2.1: (R,S_p)-Josiphos CuBr complex / diethyl ether; various solvent(s) / 0.17 h / -75 °C

2.2: 95 percent / diethyl ether; various solvent(s) / 17 h / -75 °C

3.1: Et₃SiH / palladium on carbon / CH₂Cl₂ / 20 °C

4.1: 1.491 g / CH₂Cl₂ / 24 h / Heating

With triethylsilane; palladium on activated charcoal; In diethyl ether; dichloromethane; 1.1: Wittig reaction / 4.1: Wittig reaction;

DOI:10.1021/ol071078o

upstream raw materials:

S-ethyl 2-(triphenylphosphoranylidene)ethanethioate

(S)-4-(tert-butyldiphenylsilyloxy)-3-methylbutanal

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester

(-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester

Downstream raw materials:

(-)-(3R,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexanethioic acid S-ethyl ester

(-)-(2S,4S,6S,8S,10S,12S,14S)-tert-butyl-(2,4,6,8,10,12,14-heptamethyl-triacontyloxy)-diphenyl-silane

(-)-(3R,5R,7R,9S,11S,13S,15S)-toluene-4-sulfonic acid 16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecyl ester

(-)-(3R,5R,7R,9S,11S,13S,15S)-16-(tert-butyl-diphenyl-silanyloxy)-3,5,7,9,11,13,15-heptamethyl-hexadecan-1-ol