(R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Base Information

• Chemical Name: (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol
• CAS No.: 223437-60-3
• Molecular Formula: C₄₀H₇₄O₃Si₂
• Molecular Weight: 659.197
• Mol file: 223437-60-3.mol

Synonyms:

Chemical Property of (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol

There total 9 articles about (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-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:

(E)-(20R)-de-A,B-8-(bromomethylene)cholestan-25-ol (143705-63-9) + (3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-methyl-oct-1-en-7-yne (215394-12-0) → (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol (223437-60-3)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; triethylamine; triphenylphosphine; In toluene; at 120 ℃;

DOI:10.1016/S0960-894X(97)10204-9

Reference yield:

(2S,3RS)-1-[(tert-butyldiphenylsilyl)oxy]-2-methyl-3,4-epoxybutane (223437-33-0) → (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol (223437-60-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

1.2: 41 percent / BF₃*Et₂O / tetrahydrofuran; hexane / 0.83 h / -78 °C

2.1: 98 percent / PPTS / CH₂Cl₂

3.1: 96 percent / TBAF / tetrahydrofuran / 4 h / 20 °C

4.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

5.1: CeCl₃ / tetrahydrofuran / 2 h / -78 °C

5.2: 92 percent / tetrahydrofuran / 2 h

6.1: 39 percent / TsOH*H₂O / methanol / 1 h / 20 °C

7.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

8.1: Pd₂(dba)3*CHCl₃; PPh₃; Et₃N / toluene / 6 h / Heating

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; cerium(III) chloride; oxalyl dichloride; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 4.1: Swern oxidation;

DOI:10.1021/jm000261j

Reference yield:

(2S,3R)-2-methyl-3-[(2-tetrahydropyranyl)oxy]hex-5-yn-1-ol (215394-34-6) → (R)-6-{(1R,3aS,7aR)-4-[2-[(3S,4R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4-methyl-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2-methyl-heptan-2-ol (223437-60-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: CeCl₃ / tetrahydrofuran / 2 h / -78 °C

2.2: 92 percent / tetrahydrofuran / 2 h

3.1: 39 percent / TsOH*H₂O / methanol / 1 h / 20 °C

4.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 1 h

5.1: Pd₂(dba)3*CHCl₃; PPh₃; Et₃N / toluene / 6 h / Heating

With 2,6-dimethylpyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; cerium(III) chloride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Swern oxidation;

DOI:10.1021/jm000261j

upstream raw materials:

(E)-(20R)-de-A,B-8-(bromomethylene)cholestan-25-ol

(3R,4R,5R)-3,5-bis(tert-butyldimethylsilanyloxy)-4-methyl-oct-1-en-7-yne

(2S,3R)-2-methyl-3-[(2-tetrahydropyranyl)oxy]hex-5-yn-1-ol

(2R,3R)-2-methyl-3-[(tetrahydropyranyl)oxy]hex-5-ynal