(E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester

Base Information

• Chemical Name: (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester
• CAS No.: 185099-81-4
• Molecular Formula: C₄₁H₇₂O₄Si₂
• Molecular Weight: 685.191
• Mol file: 185099-81-4.mol

Synonyms:

Chemical Property of (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester

There total 5 articles about (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl 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: 91.0%

ethyl (triphenylphosphoranylidene)acetate (1099-45-2) + (R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexanal (185099-80-3) → (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester (185099-81-4)

Guidance literature:

In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1016/S0039-128X(97)00040-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester (185099-81-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / imidazole / dimethylformamide / 2.5 h / Ambient temperature

2: 69 percent / diisobutylaluminum hydride / toluene / 3 h / -65 °C

3: 91 percent / tetrahydrofuran / 16 h / Ambient temperature

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0039-128X(97)00040-8

Reference yield:

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether (145372-43-6) → (E)-(R)-7-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-oct-2-enoic acid ethyl ester (185099-81-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / diisobutylaluminum hydride / toluene / 3 h / -65 °C

2: 91 percent / tetrahydrofuran / 16 h / Ambient temperature

With diisobutylaluminium hydride; In tetrahydrofuran; toluene;

DOI:10.1016/S0039-128X(97)00040-8

upstream raw materials:

ethyl (triphenylphosphoranylidene)acetate

(R)-5-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-hexanal

tert-butyldimethylsilyl chloride

1α-[(tert-butyldimethylsilyl)oxy]-24-(methoxycarbonyl)-25,26,27-trisnorvitamin D3 tert-butyldimethylsilyl ether

Downstream raw materials:

(E)-(R)-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-non-3-en-2-ol