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

Base Information

• Chemical Name: (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester
• CAS No.: 917590-73-9
• Molecular Formula: C₂₂H₂₈O₂SSi
• Molecular Weight: 384.615
• Mol file: 917590-73-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-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: 80.0%

S-ethyl 2-(triphenylphosphoranylidene)ethanethioate (32443-51-9) + (tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) → (E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9)

Guidance literature:

In dichloromethane; for 24h; Heating;

DOI:10.1039/b612593j

Reference yield: 96.0%

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9) + methylmagnesium bromide (75-16-1) → (-)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester (948859-72-1)

Guidance literature:

methylmagnesium bromide; With (R,S(Fe))-Josiphos/CuBr; In t-BuOMe; diethyl ether; at -78 ℃; for 0.333333h; Inert atmosphere;

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester; In t-BuOMe; diethyl ether; at -75 ℃; for 18h; Inert atmosphere;

With methanol; In t-BuOMe; diethyl ether; at -75 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/chem.201001284

Reference yield: 95.0%

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester (917590-73-9) + methylmagnesium bromide (75-16-1) → (R)-4-(tert-butyl-diphenyl-silanyloxy)-3-methyl-thiobutyric acid S-ethyl ester (917590-87-5)

Guidance literature:

methylmagnesium bromide; (S,R_Fe)-Josiphos*CuBr; In diethyl ether; at -75 ℃; for 0.333333h;

(E)-4-(tert-butyl-diphenyl-silanyloxy)-but-2-enethioic acid S-ethyl ester; In diethyl ether; at -75 ℃; for 17h;

DOI:10.1039/b612593j

upstream raw materials:

S-ethyl 2-(triphenylphosphoranylidene)ethanethioate

(tert-butyldiphenylsilanyloxy)acetaldehyde

Downstream raw materials:

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

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

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