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

Base Information

• Chemical Name: (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol
• CAS No.: 167892-94-6
• Molecular Formula: C₃₀H₅₂O₂Si
• Molecular Weight: 472.827
• Mol file: 167892-94-6.mol

Synonyms:(R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-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: 54.0%

methylmagnesium bromide (75-16-1) + 3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-93-5) → (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol (167892-94-6)

Guidance literature:

In diethyl ether; at 20 ℃; for 0.166667h;

DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene (143884-24-6) → (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol (167892-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 70 percent / dimethylsulfoxide / 0.5 h / 90 °C

2: 54 percent / DIBALH / tetrahydrofuran; hexane / -70 - 20 °C

3: 54 percent / diethyl ether / 0.17 h / 20 °C

With diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; dimethyl sulfoxide; 1: Substitution / 2: Reduction / 3: Grignard reaction;

DOI:10.1016/S0968-0896(00)00106-1

Reference yield:

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene (167892-92-4) → (R)-4-{(1R,3aS,7aR)-4-[2-[(S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol (167892-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 54 percent / DIBALH / tetrahydrofuran; hexane / -70 - 20 °C

2: 54 percent / diethyl ether / 0.17 h / 20 °C

With diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; hexane; 1: Reduction / 2: Grignard reaction;

DOI:10.1016/S0968-0896(00)00106-1

upstream raw materials:

methylmagnesium bromide

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(formylmethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

(5E,7E,20S)-3β-(tert-butyldimethylsilyloxy)-20-(p-tolylsulfonyloxymethyl)-9,10-seco-5,7,10(19)-pregnatriene

3β-[(t-butyldimethylsilyl)oxy]-20(S)-(cyanomethyl)-9,10-secopregna-5(E),7(E),10(19)-triene

Downstream raw materials:

ST₂₃₂

23-oxo-9,10-secocholesta-5(Z),7(E),10(19)-trien-1α,3β,25-triol

1α-hydroxy-3β-[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(E),7(E),10(19)-triene

1α,3β-bis[(t-butyldimethylsilyl)oxy]-20(S)-(n-propyl-23-oxo)-9,10-secopregna-5(Z),7(E),10(19)-triene