12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester

Base Information

• Chemical Name: 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester
• CAS No.: 454181-34-1
• Molecular Formula: C₃₇H₄₆O₃Si
• Molecular Weight: 566.856
• Mol file: 454181-34-1.mol

Synonyms:12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester

Chemical Property of 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester

There total 8 articles about 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic 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: 90.0%

[(S)-((E)-1-But-1-en-3-ynyl)-non-3-ynyloxy]-tert-butyl-diphenyl-silane (454181-35-2) + methyl 7-bromohept-5-ynoate (41349-38-6) → 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester (454181-34-1)

Guidance literature:

With copper(l) iodide; tetrabutylammomium bromide; potassium carbonate; In N,N-dimethyl-formamide; at -20 - 20 ℃;

DOI:10.1016/S0040-4039(02)00670-6

Reference yield:

1-Bromopentane (110-53-2) → 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester (454181-34-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / HMPA / tetrahydrofuran / 0 - 20 °C

2.1: 80 percent / HF-pyridine / tetrahydrofuran; pyridine / 20 °C

3.1: 89 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

4.1: PPh₃ / CH₂Cl₂

4.2: 77 percent / n-BuLi / tetrahydrofuran / 0 °C

5.1: 90 percent / n-Bu₄NBr; K₂CO₃; CuI / dimethylformamide / -20 - 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutylammomium bromide; potassium carbonate; pyridine hydrogenfluoride; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 4.1: Corey-Fuchs reaction;

DOI:10.1016/S0040-4039(02)00670-6

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 12-(tert-butyl-diphenyl-silanyloxy)-eicos-10-ene-5,8,14-triynoic acid methyl ester (454181-34-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / imidazole / dimethylformamide / 20 °C

2.1: 82 percent / HMPA / tetrahydrofuran / 0 - 20 °C

3.1: 80 percent / HF-pyridine / tetrahydrofuran; pyridine / 20 °C

4.1: 89 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

5.1: PPh₃ / CH₂Cl₂

5.2: 77 percent / n-BuLi / tetrahydrofuran / 0 °C

6.1: 90 percent / n-Bu₄NBr; K₂CO₃; CuI / dimethylformamide / -20 - 20 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutylammomium bromide; potassium carbonate; pyridine hydrogenfluoride; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; N,N-dimethyl-formamide; 5.1: Corey-Fuchs reaction;

DOI:10.1016/S0040-4039(02)00670-6

upstream raw materials:

[(S)-((E)-1-But-1-en-3-ynyl)-non-3-ynyloxy]-tert-butyl-diphenyl-silane

methyl 7-bromohept-5-ynoate

1-Bromopentane

tert-butylchlorodiphenylsilane

Downstream raw materials:

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