(4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal

Base Information

• Chemical Name: (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal
• CAS No.: 442550-65-4
• Molecular Formula: C₄₀H₅₈O₂Si
• Molecular Weight: 598.985
• Mol file: 442550-65-4.mol

Synonyms:(4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal

Chemical Property of (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal

There total 19 articles about (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal 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%

(4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraen-1-ol (442550-64-3) → (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal (442550-65-4)

Guidance literature:

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1016/S0968-0896(01)00402-3

Reference yield:

(2E,6E)-farnesyl acetate (4128-17-0) → (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal (442550-65-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: SeO₂; t-BuOOH

2.1: 80 percent / imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1.5 h / 0 °C

3.1: n-BuLi; N-isopropylcyclohexylamine / tetrahydrofuran; hexane / 0.17 h / -78 °C

3.2: 66 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 0.5 h / -78 °C

4.1: 83 percent / imidazole / dimethylformamide / 2 h / 0 °C

5.1: 83 percent / LiAlH₄ / diethyl ether / 2.25 h / 0 - 20 °C

6.1: sodium hydride; n-tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 10 h / 20 °C

7.1: 1.284 g / n-tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

8.1: 81 percent / imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / 0 °C

9.1: 83 percent / n-BuLi / tetrahydrofuran / 7 h / -78 °C

10.1: 84 percent / lithium triethylborohydride; bis(diphenylphosphino)propanepalladium(II) dichloride / tetrahydrofuran / 12 h / 0 °C

11.1: 100 percent / lithium; naphthalene / tetrahydrofuran / 0.5 h / -25 °C

12.1: 90 percent / pyridine-sulfur trioxide; triethylamine; DMSO / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; selenium(IV) oxide; naphthalene; bis(diphenylphosphino)propanepalladium(II) dichloride; N-cyclohexylisopropylamine; tetrabutyl ammonium fluoride; iodine; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(01)00402-3

Reference yield:

E,E,E-12-hydroxyfarnesyl acetate (93787-91-8) → (4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraenal (442550-65-4)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 80 percent / imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1.5 h / 0 °C

2.1: n-BuLi; N-isopropylcyclohexylamine / tetrahydrofuran; hexane / 0.17 h / -78 °C

2.2: 66 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.1: 83 percent / imidazole / dimethylformamide / 2 h / 0 °C

4.1: 83 percent / LiAlH₄ / diethyl ether / 2.25 h / 0 - 20 °C

5.1: sodium hydride; n-tetrabutylammonium iodide / tetrahydrofuran; dimethylformamide / 10 h / 20 °C

6.1: 1.284 g / n-tetrabutylammonium fluoride / tetrahydrofuran / 12 h / 20 °C

7.1: 81 percent / imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 1 h / 0 °C

8.1: 83 percent / n-BuLi / tetrahydrofuran / 7 h / -78 °C

9.1: 84 percent / lithium triethylborohydride; bis(diphenylphosphino)propanepalladium(II) dichloride / tetrahydrofuran / 12 h / 0 °C

10.1: 100 percent / lithium; naphthalene / tetrahydrofuran / 0.5 h / -25 °C

11.1: 90 percent / pyridine-sulfur trioxide; triethylamine; DMSO / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; naphthalene; bis(diphenylphosphino)propanepalladium(II) dichloride; N-cyclohexylisopropylamine; tetrabutyl ammonium fluoride; iodine; sulfur trioxide pyridine complex; tetra-(n-butyl)ammonium iodide; lithium; sodium hydride; lithium triethylborohydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(01)00402-3

upstream raw materials:

(4E,8E,12E,16E)-20-(tert-Butyl-diphenyl-silanyloxy)-4,8,12,17-tetramethyl-icosa-4,8,12,16-tetraen-1-ol

(2E,6E)-farnesyl acetate

<(2E)-6-Hydroxy-3-methyl-2-hexenyl>acetat

E,E,E-12-hydroxyfarnesyl acetate

Downstream raw materials:

tert-Butyl-[(4E,8E,12E,16E)-19-(3,3-dimethyl-oxiranyl)-4,9,13,17-tetramethyl-nonadeca-4,8,12,16-tetraenyloxy]-diphenyl-silane

tert-Butyl-diphenyl-[(4E,8E,12E,16E)-4,9,13,17-tetramethyl-19-(3-methyl-oxiranyl)-nonadeca-4,8,12,16-tetraenyloxy]-silane