(6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one

Base Information

• Chemical Name: (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one
• CAS No.: 916461-60-4
• Molecular Formula: C₃₃H₄₆O₂Si
• Molecular Weight: 502.813
• Mol file: 916461-60-4.mol

Synonyms:(6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one

Chemical Property of (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one

There total 17 articles about (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one 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: 90.0%

(6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-ol → (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one (916461-60-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1039/b608193m

Reference yield:

(2E,4E)-methyl 2,4,6,6-tetramethylhepta-2,4-dienoate → (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one (916461-60-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / LiAlH₄ / diethyl ether / 4 h / 0 °C

2: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

3: 74 percent / indium; La(OTf)3 / tetrahydrofuran; H₂O / 16 h / 20 °C

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

With indium; lithium aluminium tetrahydride; Dess-Martin periodane; lanthanum(lll) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1039/b608193m

Reference yield:

(2E)-2,4,4-trimethylpent-2-en-1-ol (51483-32-0) → (6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-one (916461-60-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / PCC; silica gel / CH₂Cl₂ / 3 h / 0 - 20 °C

2: 90 percent / sodium; ethanol / 12 h / 0 - 20 °C

3: 100 percent / LiAlH₄ / diethyl ether / 4 h / 0 °C

4: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

5: 74 percent / indium; La(OTf)3 / tetrahydrofuran; H₂O / 16 h / 20 °C

6: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 0 °C

With indium; lithium aluminium tetrahydride; ethanol; sodium; silica gel; Dess-Martin periodane; pyridinium chlorochromate; lanthanum(lll) triflate; In tetrahydrofuran; diethyl ether; dichloromethane; water;

DOI:10.1039/b608193m

upstream raw materials:

(2E)-2,4,4-trimethylpent-2-en-1-ol

(2E)-2,4,4-trimethylpent-2-enal

methyl 3-hydroxy-2-methylenebutyrate

methyl (E)-2,4,4-trimethylpent-2-enoate

Downstream raw materials:

anti-(4R,5R,6E,8E)-1-(tert-butyldiphenylsilyloxy)-4,6,8,10,10-pentamethyl-3-methyleneundeca-6,8-dien-5-ol