1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene

Base Information

• Chemical Name: 1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene
• CAS No.: 944276-00-0
• Molecular Formula: C₂₄H₄₄OSi
• Molecular Weight: 376.698
• Mol file: 944276-00-0.mol

Synonyms:1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene

Chemical Property of 1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene

There total 1 articles about 1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene 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: 87.0%

5,5-dimethyl-2,4-bis(prenyl)-cyclohexanone + tert-butyldimethylsilyl chloride (18162-48-6) → 1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene (944276-00-0)

Guidance literature:

With triethylamine; sodium iodide; In acetonitrile; for 2.5h; Heating;

DOI:10.1021/jo070388h

Reference yield: 57.0%

1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene (944276-00-0) + malonoyl dichloride (1663-67-8) → 5,5-dimethyl-2,4-bis(prenyl)-cyclohexanone + C21H30O3

Guidance literature:

1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene; malonoyl dichloride; In diethyl ether; at -20 ℃; for 24h;

With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In diethyl ether; water; at 20 ℃; for 6h; Further stages.;

DOI:10.1021/jo070388h

Reference yield:

1-(tert-butyldimethylsilyloxy)-5,5-dimethyl-2,4-bis(prenyl)-cyclohex-1-ene (944276-00-0) → (+/-)-(1R,5R,7S)-3-benzoyl-4-methoxy-8,8-dimethyl-5,7-bis(prenyl)-bicyclo[3.3.1]non-3-ene-2,9-dione

Guidance literature:

Multi-step reaction with 3 steps

1.1: diethyl ether / 24 h / -20 °C

1.2: KOH / benzyltriethylammonium chloride / diethyl ether; H₂O / 6 h / 20 °C

2.1: 100 mg / K₂CO₃ / acetone / 1 h / Heating

3.1: LTMP / tetrahydrofuran; hexane / 0.58 h / -78 °C

3.2: 80 percent / tetrahydrofuran; hexane / 0.5 h / -78 °C

With 2,2,6,6-tetramethylpiperidinyl-lithium; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; acetone;

DOI:10.1021/jo070388h

upstream raw materials:

tert-butyldimethylsilyl chloride