2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran

Base Information

• Chemical Name: 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran
• CAS No.: 100560-53-0
• Molecular Formula: C₃₉H₅₄O₅S
• Molecular Weight: 634.921
• Mol file: 100560-53-0.mol

Synonyms:2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran

Chemical Property of 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran

There total 20 articles about 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran 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: 88.0%

(2Z,6Z)-1-chloro-8-(benzyloxy)-2,6-dimethylocta-2,6-diene (86636-49-9) + (2Z,6Z)-1-(tetrahydropyran-2-yloxy)-2,6-dimethyl-8-(p-tolylsulfonyl)octa-2,6-diene (110547-84-7) → 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran (100560-53-0)

Guidance literature:

With sodium hydroxide; tetrabutylammomium bromide; In water; for 6h; Ambient temperature;

DOI:10.1039/c39870001036

Reference yield: 63.0%

C17H23BrO (1393475-04-1) + (2Z,6Z)-1-(tetrahydropyran-2-yloxy)-2,6-dimethyl-8-(p-tolylsulfonyl)octa-2,6-diene (110547-84-7) → 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran (100560-53-0)

Guidance literature:

C₁₇H₂₃BrO; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 1.5h; Inert atmosphere;

(2Z,6Z)-1-(tetrahydropyran-2-yloxy)-2,6-dimethyl-8-(p-tolylsulfonyl)octa-2,6-diene; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -78 ℃; for 6h; Inert atmosphere;

DOI:10.1021/ja306184m

Reference yield:

(2Z,6Z)-8-(benzyloxy)-2,6-dimethyl-1-(tetrahydropyran-2-yloxy)-octa-2,6-diene (86636-47-7) → 2-[(2Z,6Z,10Z,14Z)-16-Benzyloxy-2,6,10,14-tetramethyl-8-(toluene-4-sulfonyl)-hexadeca-2,6,10,14-tetraenyloxy]-tetrahydro-pyran (100560-53-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / Na, NH₃ / 0.17 h / -60 °C

2: MeSO₂Cl, LiCl, s-collidine / dimethylformamide / 2 h / 0 °C

3: dimethylformamide / Ambient temperature

4: 85 percent / n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -70 °C

With 2,4,6-trimethyl-pyridine; n-butyllithium; ammonia; sodium; methanesulfonyl chloride; lithium chloride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide;

DOI:10.1039/c39860001761

upstream raw materials:

(2Z,6Z)-1-chloro-8-(benzyloxy)-2,6-dimethylocta-2,6-diene

(2Z,6Z)-1-(tetrahydropyran-2-yloxy)-2,6-dimethyl-8-(p-tolylsulfonyl)octa-2,6-diene

sodium 4-methylbenzenesulfinate

(2Z,6Z)-8-(benzyloxy)-2,6-dimethyl-1-(tetrahydropyran-2-yloxy)-octa-2,6-diene

Downstream raw materials:

1-((2Z,6Z,10Z,14Z,18E,22E)-3,7,11,15,19,23,27-Heptamethyl-octacosa-2,6,10,14,18,22,26-heptaene-1-sulfonyl)-4-methyl-benzene

(2Z,6Z,10Z,14Z)-16-(Benzyloxy)-1-chloro-2,6,10,14-tetramethyl-8-(p-tolylsulfonyl)hexadeca-2,6,10,14-tetraene

(2Z,6Z,10Z,14Z,18E,22E)-3,7,11,15,19,23,27-heptamethyltriaconta-2,6,10,14,18,22,26-heptaen-1-ol

(2Z,6Z,10Z,14Z)-16-(Benzyloxy)-2,6,10,14-tetramethyl-8-(p-tolylsulfonyl)hexadeca-2,6,10,14-tetraen-1-ol