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

Base Information

• Chemical Name: 1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol
• CAS No.: 166322-50-5
• Molecular Formula: C₃₀H₄₆O₄Si
• Molecular Weight: 498.778
• Mol file: 166322-50-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol 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%

6-(tert-Butyldimethylsilanyloxy)-10-(tert-butyldiphenylsilanyloxy)-4,8-dimethoxy-5,9-dimethyldec-1-ene (166322-49-2) → 1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol (166322-50-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol;

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

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → 1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol (166322-50-5)

Guidance literature:

Multi-step reaction with 16 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

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;

DOI:10.1039/b000751j

Reference yield:

[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol (89956-14-9) → 1-(tert-Butyldiphenylsilanyloxy)-3,7-dimethoxy-2,6-dimethyldec-9-en-5-ol (166322-50-5)

Guidance literature:

Multi-step reaction with 14 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

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;

DOI:10.1039/b000751j

upstream raw materials:

6-(tert-Butyldimethylsilanyloxy)-10-(tert-butyldiphenylsilanyloxy)-4,8-dimethoxy-5,9-dimethyldec-1-ene

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:

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

(E)-(3R,4R,5S,9S,10R,12R,13S,14R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-17-(4-hydroxymethyl-[2,4';2',4'']teroxazol-2''-yl)-10,14-dimethoxy-12-methoxymethoxy-3,5,9,13-tetramethyl-heptadec-16-en-6-ol