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

Base Information

Chemical Name:1-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-7-en-6-one
CAS No.:166322-64-1
Molecular Formula:C₃₉H₇₀O₉Si
Molecular Weight:711.065
Hs Code.:

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

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

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Purity/Quality:: 98% ^*data from raw suppliers

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

There total 35 articles about 1-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-7-en-6-one 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%

: 166322-55-0
3,7,9,9-Tetramethoxy-5-methoxomethoxy-2,6-dimethylnonanal

: 166322-63-0
[7-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-2-oxoheptyl]phosphonic acid dimethyl ester

: 166322-64-1
1-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-7-en-6-one

Guidance literature:: With barium dihydroxide; In tetrahydrofuran; water;
DOI:10.1016/0040-4039(95)00955-C

Reference yield:

: 70542-83-5
ethyl (2E)-5-(benzyloxy)pent-2-enoate

: 166322-64-1
1-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-7-en-6-one

Guidance literature:: Multi-step reaction with 14 steps

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

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

2.2: 76 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -20 - -18 °C

3.1: CH₂Cl₂ / 15 h / 0 - 20 °C

4.1: aq. NaIO₄ / methanol / 6 h

5.1: 94 percent / CH₂Cl₂ / 20 °C

6.1: 96 percent / DIBAL-H / hexane; tetrahydrofuran / 2 h / 0 °C

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

7.2: 85 percent / t-BuOOH / CH₂Cl₂ / 20 h / -20 - -18 °C

8.1: CuI / tetrahydrofuran / 0.5 h / 0 °C

8.2: tetrahydrofuran / 15 h / 5 °C

8.3: 84 percent / aq. NaIO₄ / methanol / 7 h

9.1: 97.5 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

10.1: 96 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂; methanol / 8 h / 20 °C

11.1: 96 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropyl ammonium perruthenate / CH₂Cl₂ / 1.25 h / 20 °C

12.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

12.2: 90 percent / hexane; tetrahydrofuran / 1 h / -78 °C

13.1: 92 percent / pyridinium dichromate / dimethylformamide / 24 h / 20 °C

14.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

14.2: 95 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

With 2,6-dimethylpyridine; barium dihydroxide; sodium periodate; copper(l) iodide; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; (+)-Weinsaeure-diethylester; (-)-diethyl tartrate; titanium(IV) isopropylate; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Substitution / 2.2: Epoxidation / 3.1: Methylation / 4.1: Oxidation / 5.1: Condensation / 6.1: Reduction / 7.1: Substitution / 7.2: Epoxidation / 8.1: Transmetallation / 8.2: Methylation / 8.3: Oxidation / 9.1: Substitution / 10.1: Substitution / 11.1: Oxidation / 12.1: Metallation / 12.2: Addition / 13.1: Oxidation / 14.1: Hydrolysis / 14.2: Condensation;
DOI:10.1039/b000751j

Reference yield:

: 89923-31-9
(E)-5-(benzyloxy)pent-2-en-1-ol

: 166322-64-1
1-Benzyloxy-4-(tert-butyldimethylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-7-en-6-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: (+)-diethyl tartrate; 4-Angstroem molecular sieves / Ti(OiPr)4 / CH₂Cl₂ / 0.5 h / -20 °C

1.2: 76 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / 20 h / -20 - -18 °C

2.1: CH₂Cl₂ / 15 h / 0 - 20 °C

3.1: aq. NaIO₄ / methanol / 6 h

4.1: 94 percent / CH₂Cl₂ / 20 °C

5.1: 96 percent / DIBAL-H / hexane; tetrahydrofuran / 2 h / 0 °C

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

6.2: 85 percent / t-BuOOH / CH₂Cl₂ / 20 h / -20 - -18 °C

7.1: CuI / tetrahydrofuran / 0.5 h / 0 °C

7.2: tetrahydrofuran / 15 h / 5 °C

7.3: 84 percent / aq. NaIO₄ / methanol / 7 h

8.1: 97.5 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

9.1: 96 percent / pyridinium toluene-p-sulfonate / CH₂Cl₂; methanol / 8 h / 20 °C

10.1: 96 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetrapropyl ammonium perruthenate / CH₂Cl₂ / 1.25 h / 20 °C

11.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

11.2: 90 percent / hexane; tetrahydrofuran / 1 h / -78 °C

12.1: 92 percent / pyridinium dichromate / dimethylformamide / 24 h / 20 °C

13.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

13.2: 95 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

With 2,6-dimethylpyridine; barium dihydroxide; sodium periodate; copper(l) iodide; dipyridinium dichromate; n-butyllithium; 4 A molecular sieve; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; (+)-Weinsaeure-diethylester; (-)-diethyl tartrate; titanium(IV) isopropylate; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Epoxidation / 2.1: Methylation / 3.1: Oxidation / 4.1: Condensation / 5.1: Reduction / 6.1: Substitution / 6.2: Epoxidation / 7.1: Transmetallation / 7.2: Methylation / 7.3: Oxidation / 8.1: Substitution / 9.1: Substitution / 10.1: Oxidation / 11.1: Metallation / 11.2: Addition / 12.1: Oxidation / 13.1: Hydrolysis / 13.2: Condensation;
DOI:10.1039/b000751j