(1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol

Base Information

• Chemical Name: (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol
• CAS No.: 119947-82-9
• Molecular Formula: C₂₆H₄₆O₃Si
• Molecular Weight: 434.735
• Mol file: 119947-82-9.mol

Synonyms:(1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol

Chemical Property of (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol

There total 8 articles about (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol 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%

(1E,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,7-dien-4-yne-3,6-diol (118272-49-4,118304-61-3) → (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol (119947-82-9)

Guidance literature:

With hydrogen; Lindlar's catalyst;

DOI:10.1016/S0040-4039(00)80055-6

Reference yield: 80.0%

triethylsilyl chloride (994-30-9) + (2Z,5Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,5,8-triene-1,4,7-triol (119996-77-9) → (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol (119947-82-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 18h; Ambient temperature;

DOI:10.1021/jo00272a032

Reference yield:

5-hydroxy-4-methyl-5H-furan-2-one (40834-42-2) → (1E,4Z,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,4,7-triene-3,6-diol (119947-82-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) HMPA, 0 deg C, 1 h, 2.) 20 min

2: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min

3: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C

4: 90 percent / H₂ / Lindlar catalyst / methanol / 24 h

5: 80 percent / imidazole / dimethylformamide / 18 h / Ambient temperature

With 1H-imidazole; ethylmagnesium bromide; hydrogen; sodium hydride; diisobutylaluminium hydride; Lindlar's catalyst; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00272a032

upstream raw materials:

triethylsilyl chloride

(2Z,5Z,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,5,8-triene-1,4,7-triol

(1E,7Z)-3,7-Dimethyl-9-triethylsilanyloxy-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-1,7-dien-4-yne-3,6-diol

5-hydroxy-4-methyl-5H-furan-2-one

Downstream raw materials:

ethyl 13-cis-retinoate

13-cis-vitamin A aldehyde

2-cis-Vitamin-A

13-cis-retinoic acid