(2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate

Base Information

• Chemical Name: (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate
• CAS No.: 1402974-90-6
• Molecular Formula: C₂₉H₄₃F₅O₃Si
• Molecular Weight: 562.736
• Mol file: 1402974-90-6.mol

Synonyms:(2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate

Chemical Property of (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate

There total 11 articles about (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate 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: 85.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + (2S,4S,6E,8R,9R,10E)-9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoic acid (1402974-89-3) → (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate (1402974-90-6)

Guidance literature:

2,3,4,5,6-pentafluorophenol; With dicyclohexyl-carbodiimide; In ethyl acetate; at 0 ℃; for 0.5h; Inert atmosphere;

(2S,4S,6E,8R,9R,10E)-9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoic acid; In ethyl acetate; at 0 - 20 ℃; for 9.5h; Inert atmosphere;

DOI:10.1002/chem.201201879 DOI:10.1002/chem.201201879

Reference yield:

(R)-4-benzyl-3-((2S,4S,6E,8R,9R,10E)-9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoyl)oxazolidin-2-one (1402974-88-2) → (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate (1402974-90-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dihydrogen peroxide; lithium hydroxide monohydrate; water / tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere

2.1: dicyclohexyl-carbodiimide / ethyl acetate / 0.5 h / 0 °C / Inert atmosphere

2.2: 9.5 h / 0 - 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; water; dihydrogen peroxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethyl acetate;

DOI:10.1002/chem.201201879 DOI:10.1002/chem.201201879

Reference yield:

2-methylbut-2-enal (497-03-0) → (2S,4S,6E,8R,9R,10E)-perfluorophenyl 9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoate (1402974-90-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: titanium tetrachloride / dichloromethane / 120 h / -78 - -50 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 - 20 °C / Inert atmosphere

3.1: lithium borohydride / methanol; diethyl ether / 4 h / 0 - 20 °C / Inert atmosphere

4.1: methyltriphenoxyphosphonium iodide / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C / Inert atmosphere

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -80 °C / Inert atmosphere

5.2: 18 h / -80 - -50 °C / Inert atmosphere

6.1: lithium borohydride / methanol; diethyl ether / 4 h / 0 °C / Inert atmosphere

7.1: pyridine / dichloromethane / 0.08 h / -78 °C

7.2: 0.58 h / -78 - 20 °C / Inert atmosphere

8.1: 1,1,1,3,3,3-hexamethyldisilazane alkali metal salt / tetrahydrofuran / 1 h / -80 °C / Inert atmosphere

8.2: 18 h / -80 - -50 °C / Inert atmosphere

9.1: dihydrogen peroxide; lithium hydroxide monohydrate; water / tetrahydrofuran / 15 h / 0 - 20 °C / Inert atmosphere

10.1: dicyclohexyl-carbodiimide / ethyl acetate / 0.5 h / 0 °C / Inert atmosphere

10.2: 9.5 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,6-dimethylpyridine; lithium borohydride; lithium hydroxide monohydrate; methyltriphenoxyphosphonium iodide; water; dihydrogen peroxide; sodium hexamethyldisilazane; titanium tetrachloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: |Mukaiyama Aldol Addition;

DOI:10.1002/chem.201201879 DOI:10.1002/chem.201201879

upstream raw materials:

(R)-4-benzyl-3-((2S,4S,6E,8R,9R,10E)-9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoyl)oxazolidin-2-one

2,3,4,5,6-pentafluorophenol

(2S,4S,6E,8R,9R,10E)-9-(tert-butyldimethylsilyloxy)-2,4,6,8,10-pentamethyldodeca-6,10-dienoic acid

(S)-4-benzyl-3-((2R,4E,6R,7R,8E)-7-(tert-butyldimethylsilyloxy)-2,4,6,8-tetramethyldeca-4,8-dienoyl)oxazolidin-2-one