(2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol

Base Information

• Chemical Name: (2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol
• CAS No.: 1068574-72-0
• Molecular Formula: C₂₆H₃₆O₂Si
• Molecular Weight: 408.656
• Mol file: 1068574-72-0.mol

Synonyms:(2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol

Chemical Property of (2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol

There total 2 articles about (2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-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: 86.0%

(2E)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-one (1068574-62-8) → (2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol (1068574-72-0)

Guidance literature:

With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; In tetrahydrofuran; toluene; at -60 ℃; for 36h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201001315

Reference yield:

(Δ2,3E)-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1,4-diol → (2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol (1068574-72-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 15 h / 20 °C

2: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole / tetrahydrofuran; toluene / 36 h / -60 °C / Inert atmosphere

With (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; benzo[1,3,2]dioxaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide; toluene;

DOI:10.1002/ejoc.201001315

Reference yield: 85.0%

(2E,4S)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-ol (1068574-72-0) + acetic anhydride (108-24-7) → (2E,4S)-1-(tert-butyldiphenylsilyloxy)-3,7-dimethylocta-2,6-dien-4-yl acetate (1068574-67-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 17h;

DOI:10.1002/ejoc.201001315

upstream raw materials:

(2E)-1-(tert-butyldiphenylsilanyloxy)-3,7-dimethylocta-2,6-dien-4-one

Downstream raw materials:

(2E,4S,6E)-1-(tert-butyldiphenylsilanyloxy)-8-hydroxy-3,7-dimethylocta-2,6-dien-4-yl acetate

(2E,4S,6E)-1-[(tert-butyldiphenylsilanyl)oxy]-3,7-dimethyl-8-oxoocta-2,6-dien-4-yl acetate

(2E,5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethylocta-2,6-diene-1,5-diyl diacetate

(5S,6E)-8-[(tert-butyldiphenylsilanyl)oxy]-2,6-dimethyloct-6-ene-2,5-diol