(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-ol

Base Information

Chemical Name:(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-ol
CAS No.:503071-56-5
Molecular Formula:C₃₄H₄₈O₂Si
Molecular Weight:516.839
Hs Code.:

Synonyms:(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-ol

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Chemical Property of (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-ol

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Technology Process of (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-ol

There total 12 articles about (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-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: 94.0%

: 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

: 503071-56-5
(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-ol

Guidance literature:: With potassium carbonate; In methanol;
DOI:10.1016/S0040-4039(02)02646-1

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 503071-56-5
(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-ol

Guidance literature:: Multi-step reaction with 10 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

10.1: 94 percent / K₂CO₃ / methanol / 15 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; potassium carbonate; acetic acid; triethylamine; (-)-B-methoxy-diisopinocamphenylborane; 1,3-bis(2,4,6-triMePh)imidazolidine based ruthenium catalyst; In tetrahydrofuran; methanol; 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

: 503071-56-5
(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-ol

Guidance literature:: Multi-step reaction with 11 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

11.1: 94 percent / K₂CO₃ / methanol / 15 h / 20 °C

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