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

Base Information

Chemical Name:4-(tert-Butyldimethylsilanyloxy)-1-(tert-butyldiphenylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-6-one
CAS No.:203520-13-2
Molecular Formula:C₄₈H₈₄O₉Si₂
Molecular Weight:861.361
Hs Code.:

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

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

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

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

There total 35 articles about 4-(tert-Butyldimethylsilanyloxy)-1-(tert-butyldiphenylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-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: 94.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 301230-16-0
4-(tert-Butyldimethylsilanyloxy)-1-hydroxy-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-6-one

: 203520-13-2
4-(tert-Butyldimethylsilanyloxy)-1-(tert-butyldiphenylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-6-one

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 14h;
DOI:10.1039/b000751j

Reference yield:

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

: 203520-13-2
4-(tert-Butyldimethylsilanyloxy)-1-(tert-butyldiphenylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-6-one

Guidance literature:: Multi-step reaction with 24 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

19.1: 98 percent / p-TsOH / methanol / 1 h / 20 °C

20.1: 98 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

21.1: 89 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / TPAP / CH₂Cl₂ / 1 h / 20 °C

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

22.2: 95 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

23.1: 94 percent / H₂ / Pearlman's catalyst / methanol

24.1: 94 percent / imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; barium dihydroxide; copper(l) iodide; lithium borohydride; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; palladium dihydroxide; tetrapropylammonium perruthennate; 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 / 19.1: Addition / 20.1: Substitutio;
DOI:10.1039/b000751j

Reference yield:

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

: 203520-13-2
4-(tert-Butyldimethylsilanyloxy)-1-(tert-butyldiphenylsilanyloxy)-10,14,16,16-tetramethoxy-12-methoxymethoxy-3,5,9,13-tetramethylhexadec-6-one

Guidance literature:: Multi-step reaction with 23 steps

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

1.2: 61 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

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

2.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

3.1: 94 percent / imidazole / dimethylformamide / 20 °C

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

4.2: 66 percent / dimethylformamide / 2 h / 20 °C

5.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

6.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

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

7.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

8.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

9.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

10.1: 82 percent / LiBH₄ / methanol; tetrahydrofuran / 1.5 h / 0 °C

11.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

12.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

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

13.2: 70 percent / diethyl ether / 5 h / -78 °C

14.1: 95 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 1.17 h / Heating

15.1: 90 percent / pyridinium toluene-p-sulfonate / ethanol / 9 h / Heating

16.1: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 3 h / Heating

17.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

17.2: 89 percent / PPh₃ / CH₂Cl₂ / 0.25 h / -78 °C

18.1: 98 percent / p-TsOH / methanol / 1 h / 20 °C

19.1: 98 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

20.1: 89 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / TPAP / CH₂Cl₂ / 1 h / 20 °C

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

21.2: 95 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

22.1: 94 percent / H₂ / Pearlman's catalyst / methanol

23.1: 94 percent / imidazole / dimethylformamide / 14 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; barium dihydroxide; copper(l) iodide; lithium borohydride; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; palladium dihydroxide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: Epoxidation / 2.1: Transmetallation / 2.2: Methylation / 3.1: Substitution / 4.1: Metallation / 4.2: Methylation / 5.1: Hydrogenolysis / 6.1: Oxidation / 7.1: Addition / 7.2: Condensation / 8.1: Reduction / 9.1: Substitution / 10.1: Reduction / 11.1: Substitution / 12.1: Oxidation / 13.1: Addition / 13.2: Addition / 14.1: Etherification / 15.1: Substitution / 16.1: Etherification / 17.1: Oxidation / 17.2: Elimination / 18.1: Addition / 19.1: Substitution / 20.1: Oxidatio;
DOI:10.1039/b000751j