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

Base Information

• Chemical Name: 9-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxomethoxy-4,8-dimethylnonanal
• CAS No.: 166322-52-7
• Molecular Formula: C₃₁H₄₈O₆Si
• Molecular Weight: 544.804

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 18 articles about 9-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxomethoxy-4,8-dimethylnonanal 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: 89.0%

tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane (166322-51-6) → 9-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxomethoxy-4,8-dimethylnonanal (166322-52-7)

Guidance literature:

tert-Butyl(3,7-dimethoxy-5-methoxomethoxy-2,6-dimethyldec-9-enyloxy)diphenylsilane; With ozone; In dichloromethane; at -78 ℃; for 0.166667h;

With triphenylphosphine; In dichloromethane; at -78 ℃; for 0.25h; Further stages.;

DOI:10.1039/b000751j

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → 9-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxomethoxy-4,8-dimethylnonanal (166322-52-7)

Guidance literature:

Multi-step reaction with 18 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

18.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

18.2: 89 percent / PPh₃ / CH₂Cl₂ / 0.25 h / -78 °C

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 / 18.1: Oxidation / 18.2: Elimination;

DOI:10.1039/b000751j

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → 9-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxomethoxy-4,8-dimethylnonanal (166322-52-7)

Guidance literature:

Multi-step reaction with 16 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

16.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

16.2: 89 percent / PPh₃ / CH₂Cl₂ / 0.25 h / -78 °C

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 / 16.1: Oxidation / 16.2: Elimination;

DOI:10.1039/b000751j

upstream raw materials:

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

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

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

(E)-5-(benzyloxy)pent-2-en-1-ol

Downstream raw materials:

tert-Butyl(3,7,9,9-tetramethoxy-5-methoxymethoxy-2,6-dimethylnonyloxy)diphenylsilane

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

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