tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane

Base Information

• Chemical Name: tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane
• CAS No.: 166322-51-6
• Molecular Formula: C₃₂H₅₀O₅Si
• Molecular Weight: 542.832
• Mol file: 166322-51-6.mol

Synonyms:tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane

Chemical Property of tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane

There total 17 articles about tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane 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: 95.0%

chloromethyl methyl ether (107-30-2) + 1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol (166322-50-5) → tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane (166322-51-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine;

DOI:10.1016/0040-4039(95)00955-C

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane (166322-51-6)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: Ti(O-i-Pr)4; (-)-diethyl tartrate; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

2.2: 61 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

3.1: CuI / tetrahydrofuran / 0.5 h / -20 °C

3.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

4.1: 94 percent / imidazole / dimethylformamide / 20 °C

5.1: NaH / dimethylformamide / 0.08 h / 0 °C

5.2: 66 percent / dimethylformamide / 2 h / 20 °C

6.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

7.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

8.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

8.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

9.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

10.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 82 percent / LiBH₄ / methanol; tetrahydrofuran / 1.5 h / 0 °C

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

13.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

14.1: (+)-IPC₂BOMe / diethyl ether / 2 h / -78 - 20 °C

14.2: 70 percent / diethyl ether / 5 h / -78 °C

15.1: 95 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 1.17 h / Heating

16.1: 90 percent / pyridinium toluene-p-sulfonate / ethanol / 9 h / Heating

17.1: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 3 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; copper(l) iodide; lithium borohydride; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; ozone; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Substitution / 2.2: Epoxidation / 3.1: Transmetallation / 3.2: Methylation / 4.1: Substitution / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrogenolysis / 7.1: Oxidation / 8.1: Addition / 8.2: Condensation / 9.1: Reduction / 10.1: Substitution / 11.1: Reduction / 12.1: Substitution / 13.1: Oxidation / 14.1: Addition / 14.2: Addition / 15.1: Etherification / 16.1: Substitution / 17.1: Etherification;

DOI:10.1039/b000751j

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane (166322-51-6)

Guidance literature:

Multi-step reaction with 15 steps

1.1: CuI / tetrahydrofuran / 0.5 h / -20 °C

1.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

2.1: 94 percent / imidazole / dimethylformamide / 20 °C

3.1: NaH / dimethylformamide / 0.08 h / 0 °C

3.2: 66 percent / dimethylformamide / 2 h / 20 °C

4.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

5.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

6.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

6.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

7.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

8.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

9.1: 82 percent / LiBH₄ / methanol; tetrahydrofuran / 1.5 h / 0 °C

10.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

12.1: (+)-IPC₂BOMe / diethyl ether / 2 h / -78 - 20 °C

12.2: 70 percent / diethyl ether / 5 h / -78 °C

13.1: 95 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 1.17 h / Heating

14.1: 90 percent / pyridinium toluene-p-sulfonate / ethanol / 9 h / Heating

15.1: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 3 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; copper(l) iodide; lithium borohydride; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Transmetallation / 1.2: Methylation / 2.1: Substitution / 3.1: Metallation / 3.2: Methylation / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Addition / 6.2: Condensation / 7.1: Reduction / 8.1: Substitution / 9.1: Reduction / 10.1: Substitution / 11.1: Oxidation / 12.1: Addition / 12.2: Addition / 13.1: Etherification / 14.1: Substitution / 15.1: Etherification;

DOI:10.1039/b000751j

upstream raw materials:

chloromethyl methyl ether

1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol

ethyl (2E)-5-(benzyloxy)pent-2-enoate

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

Downstream raw materials:

9-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxomethoxy-4,8-dimethylnonanal

1-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-7-en-6-one

4-(tert-Butyldimethylsilanyloxy)-1-(tert-butyldiphenylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-6-one

13-(tert-Butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxymethoxy-4,8,12,14-tetramethyl-11-oxohexadecanal