acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

Base Information

Chemical Name:acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester
CAS No.:402827-34-3
Molecular Formula:C₃₆H₅₀O₃Si
Molecular Weight:558.877
Hs Code.:

acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

Synonyms:acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

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Chemical Property of acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

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Technology Process of acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

There total 11 articles about acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester 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: 88.0%

: 402827-33-2
acetic acid (1R)-1-[{(1R,2R,6R)-2-[(2R)-2-(tert-butyl(diphenyl)silanyloxy)pent-4-enyl]-6-isopropyl-3-methylcyclohex-3-enyl}methyl]but-3-enyl ester

: 402827-34-3
acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 168h;
DOI:10.1016/S0040-4039(01)02045-7

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 402827-34-3
acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 100 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

2.1: 99 percent / AcOH / H₂O; tetrahydrofuran / 21 h / 20 °C

3.1: 98 percent / NaBH₄ / ethanol / 0.25 h / 20 °C

4.1: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

5.1: 95 percent / 18-crown-6 / acetonitrile / 6 h / 80 °C

6.1: DIBAL-H / toluene; hexane / 0.75 h / -78 °C

6.2: 100 percent / tartaric acid / H₂O; ethyl acetate; various solvents / 1 h / 20 °C

7.1: ¹Ipc₂BOMe / tetrahydrofuran; diethyl ether / 1 h / 20 °C

7.2: tetrahydrofuran; diethyl ether / 3 h / -78 °C

7.3: 55 percent / H₂O₂; NaOH / H₂O; tetrahydrofuran; diethyl ether / 0.67 h / 20 °C

8.1: 94 percent / pyridine; 4-(dimethylamino)pyridine / 24 h / 20 °C

9.1: 88 percent / 1,3-bis(2,4,6-triMePh)imidazolidine based ruthenium catalyst / CH₂Cl₂ / 120 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; acetic acid; triethylamine; (-)-B-methoxy-diisopinocamphenylborane; 1,3-bis(2,4,6-triMePh)imidazolidine based ruthenium catalyst; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 7.2: Brown allylation;
DOI:10.1016/j.tet.2003.08.057

Reference yield:

: 221290-57-9
[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetaldehyde

: 402827-34-3
acetic acid (4R,4aR,6R,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: ¹Ipc₂BOMe / diethyl ether; tetrahydrofuran / 1 h / 20 °C

1.2: diethyl ether; tetrahydrofuran / 6 h / -78 °C

1.3: 77 percent / H₂O₂; NaOH / H₂O; tetrahydrofuran; diethyl ether / 15 h / 20 °C

2.1: 100 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

3.1: 99 percent / AcOH / H₂O; tetrahydrofuran / 21 h / 20 °C

4.1: 98 percent / NaBH₄ / ethanol / 0.25 h / 20 °C

5.1: 100 percent / Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

6.1: 95 percent / 18-crown-6 / acetonitrile / 6 h / 80 °C

7.1: DIBAL-H / toluene; hexane / 0.75 h / -78 °C

7.2: 100 percent / tartaric acid / H₂O; ethyl acetate; various solvents / 1 h / 20 °C

8.1: ¹Ipc₂BOMe / tetrahydrofuran; diethyl ether / 1 h / 20 °C

8.2: tetrahydrofuran; diethyl ether / 3 h / -78 °C

8.3: 55 percent / H₂O₂; NaOH / H₂O; tetrahydrofuran; diethyl ether / 0.67 h / 20 °C

9.1: 94 percent / pyridine; 4-(dimethylamino)pyridine / 24 h / 20 °C

10.1: 88 percent / 1,3-bis(2,4,6-triMePh)imidazolidine based ruthenium catalyst / CH₂Cl₂ / 120 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; acetic acid; triethylamine; (-)-B-methoxy-diisopinocamphenylborane; 1,3-bis(2,4,6-triMePh)imidazolidine based ruthenium catalyst; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 1.2: Brown allylation / 8.2: Brown allylation;
DOI:10.1016/j.tet.2003.08.057