(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

Base Information

Chemical Name:(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester
CAS No.:849122-86-7
Molecular Formula:C₄₈H₆₀N₂O₅Si
Molecular Weight:773.1
Hs Code.:

(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

Synonyms:(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

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Chemical Property of (E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

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Technology Process of (E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

There total 12 articles about (E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-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: 82.0%

: 198336-17-3
pivaloyl N-methylurocanate

: 634151-80-7
(Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-ol

: 849122-86-7
(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

Guidance literature:: With dmap; TEA; In 1,2-dichloro-ethane; at 80 ℃; for 6h;
DOI:10.1016/j.tet.2004.12.039

Reference yield:

: 848760-88-3
(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]3-(4-methoxyphenoxy)-pent-4-en-2-ol

: 849122-86-7
(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: 95 percent / DIPEA; TBAI / CH₂Cl₂ / 7 h / 25 °C

2.1: LiBF₄ / acetonitrile; H₂O / 6 h / 25 °C

3.1: 408 mg / NaBH₄ / ethanol / 0.33 h / 25 °C

4.1: 95 percent / TEA / CH₂Cl₂ / 0 - 25 °C

5.1: 100 percent / 18-crown-6 / acetonitrile / 2.5 h / 80 °C

6.1: DIBAL-H / hexane; toluene / 1 h / -78 °C

7.1: 420 mg / tetrahydrofuran; diethyl ether / 48 h / -78 °C

8.1: 90 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

9.1: 45 percent / Me₂S; BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -20 °C

10.1: Grubbs catalyst / benzene / 19 h / 80 °C

10.2: 80 percent / benzene; dimethylsulfoxide / 12 h / 20 °C

11.1: 82 percent / TEA; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 6 h / 80 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium tetrafluoroborate; 18-crown-6 ether; dimethylsulfide; TEA; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; benzene; 7.1: Brown allylation;
DOI:10.1016/j.tet.2004.12.039

Reference yield:

: 849122-81-2
(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-(4-methoxyphenoxy)-pent-4-enyl]-3-methyl-cyclohex-3-enecarbaldehyde

: 849122-86-7
(E)-3-(1-methyl-1H-imidazol-4-yl)-acrylic acid (Z)-(1R,4aR,6S,7R,11S,12aR)-11-(tert-butyl-diphenylsilanyloxy)-1-isopropyl-7-(4-methoxyphenoxy)-4-methyl-1,2,4a,5,6,7,10,11,12,12a-decahydro-benzocyclodecen-6-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 408 mg / NaBH₄ / ethanol / 0.33 h / 25 °C

2.1: 95 percent / TEA / CH₂Cl₂ / 0 - 25 °C

3.1: 100 percent / 18-crown-6 / acetonitrile / 2.5 h / 80 °C

4.1: DIBAL-H / hexane; toluene / 1 h / -78 °C

5.1: 420 mg / tetrahydrofuran; diethyl ether / 48 h / -78 °C

6.1: 90 percent / imidazole / CH₂Cl₂ / 16 h / 20 °C

7.1: 45 percent / Me₂S; BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / -20 °C

8.1: Grubbs catalyst / benzene / 19 h / 80 °C

8.2: 80 percent / benzene; dimethylsulfoxide / 12 h / 20 °C

9.1: 82 percent / TEA; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 6 h / 80 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; 18-crown-6 ether; dimethylsulfide; TEA; boron trifluoride diethyl etherate; diisobutylaluminium hydride; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; 1,2-dichloro-ethane; toluene; acetonitrile; benzene; 5.1: Brown allylation;
DOI:10.1016/j.tet.2004.12.039