(E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester

Base Information

• Chemical Name: (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester
• CAS No.: 90108-31-9
• Molecular Formula: C₂₇H₃₃BrO₃Si
• Molecular Weight: 513.547
• Mol file: 90108-31-9.mol

Synonyms:(E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester

Chemical Property of (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester

There total 6 articles about (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl 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: 92.0%

methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate (90108-30-8) → (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester (90108-31-9)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at -40 - 0 ℃;

DOI:10.1021/ja00324a024

Reference yield:

methyl 4-(chlorocarbonyl)butyrate (1501-26-4) → (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester (90108-31-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 60 percent / AlCl₃ / CH₂Cl₂ / 0 °C

2: 85 percent / (-)-9-pinanyl-BBN / tetrahydrofuran / 25 °C

3: 80 percent / KF_.2H₂O / dimethylformamide

4: 96 percent / imidazole / dimethylformamide

5: 93 percent / Et₂NH, Pd(PPh₃)4, CuI / 15 h / Ambient temperature

6: 92 percent / PPh₃, CBr₄ / CH₂Cl₂ / -40 - 0 °C

With 1H-imidazole; potassium fluoride; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; aluminium trichloride; carbon tetrabromide; (-)-9-pinanyl-BBN; diethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00324a024

Reference yield:

(5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester (90108-29-5) → (E)-(S)-10-Bromo-5-(tert-butyl-diphenyl-silanyloxy)-dec-8-en-6-ynoic acid methyl ester (90108-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / Et₂NH, Pd(PPh₃)4, CuI / 15 h / Ambient temperature

2: 92 percent / PPh₃, CBr₄ / CH₂Cl₂ / -40 - 0 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; carbon tetrabromide; diethylamine; triphenylphosphine; In dichloromethane;

DOI:10.1021/ja00324a024

upstream raw materials:

methyl 5(S)-(tert-butyldiphenylsiloxy)-10-hydroxydec-8-en-6-ynoate

methyl 4-(chlorocarbonyl)butyrate

(5S)-5-t-butyl diphenyl silyloxy-hept-6-ynoic acid, methyl ester

(5S)-5-hydroxy-hept-6-ynoic acid, methyl ester

Downstream raw materials:

(2R)-2-<(tert-butyldiphenylsilyl)oxy>-4-decyn-1-ol

(8E,10E,14Z)-(5S,12R)-5,12-Bis-(tert-butyl-diphenyl-silanyloxy)-icosa-8,10,14-trien-6-ynoic acid methyl ester

(5S,8E,10E,12R)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-8,10-eicosadiene-6,14-diynoate

(5S,6Z,8E,10E,12R,14Z)-methyl 5,12-bis<(tert-butyldiphenylsilyl)oxy>-6,8,10,14-eicosatetraenoate