(1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

Base Information

Chemical Name:(1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane
CAS No.:503071-60-1
Molecular Formula:C₃₅H₄₈OSi
Molecular Weight:512.851
Hs Code.:

Synonyms:(1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

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Chemical Property of (1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

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Technology Process of (1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

There total 15 articles about (1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane 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%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 503071-57-6
(4R,4aR,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4a,5,7,10,11,12,12a-octahydro-4H-benzocyclodecen-6-one

: 503071-60-1
(1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

Guidance literature:: Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at 20 ℃; for 1h;

(4R,4aR,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4a,5,7,10,11,12,12a-octahydro-4H-benzocyclodecen-6-one; In tetrahydrofuran; hexane; at 50 ℃; for 12h;
DOI:10.1016/j.tet.2003.08.057

Reference yield: 92.0%

: 19493-09-5
Methylenetriphenylphosphorane

: 503071-57-6
(4R,4aR,11R,12aR)-11-(tert-butyl(diphenyl)silanyloxy)-4-isopropyl-1-methyl-3,4a,5,7,10,11,12,12a-octahydro-4H-benzocyclodecen-6-one

: 503071-60-1
(1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

Guidance literature:: In tetrahydrofuran; at 50 ℃;
DOI:10.1016/S0040-4039(02)02646-1

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 503071-60-1
(1R,4aR,6R,12aR)-tert-butyl(1-isopropyl-4-methyl-11-methylene-1,2,4a,5,6,7,10,11,12,12a-decahydrobenzocyclodecen-6-yloxy)diphenylsilane

Guidance literature:: Multi-step reaction with 12 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

11.1: 81 percent / (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 1.83 h / -60 - 0 °C

12.1: n-BuLi / hexane; tetrahydrofuran / 1 h / 20 °C

12.2: 94 percent / tetrahydrofuran; hexane / 12 h / 50 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; 18-crown-6 ether; diisobutylaluminium hydride; potassium carbonate; acetic acid; dimethyl sulfoxide; 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