Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

Base Information

• Chemical Name: Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester
• CAS No.: 445389-07-1
• Molecular Formula: C₂₉H₄₂O₆S
• Molecular Weight: 518.715
• Mol file: 445389-07-1.mol

Synonyms:Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

Chemical Property of Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

There total 4 articles about Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester 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: 85.0%

sodium benzenesulfonate (873-55-2) + Carbonic acid (2E,6E)-9-(2-bromo-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester (445389-06-0) → Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester (445389-07-1)

Guidance literature:

In N,N-dimethyl-formamide; at 23 ℃; for 18h;

DOI:10.1021/ol026205p

Reference yield:

tert-butyl-(5-isopropyl-1,2-dimethyl-hexa-1,5-dienyloxy)-dimethyl-silane → Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester (445389-07-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / (Me₂N)3S⁽¹⁺⁾Me₃SiF₂^(1-) / tetrahydrofuran; dimethylformamide / 2.5 h / -30 - 0 °C

2: iPr₂NEt / CH₂Cl₂ / 1.5 h / 0 °C

3: 92 percent / NBS; NaHCO₃ / tetrahydrofuran / 2 h / -78 °C

4: 85 percent / dimethylformamide / 18 h / 23 °C

With N-Bromosuccinimide; tris(dimethylamino)sulfonium trimethylsilyldifluoride; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol026205p

Reference yield:

Carbonic acid (2E,6E)-9-acetyl-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester (445389-04-8) → Carbonic acid (2E,6E)-9-(2-benzenesulfonyl-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester (445389-07-1)

Guidance literature:

Multi-step reaction with 3 steps

1: iPr₂NEt / CH₂Cl₂ / 1.5 h / 0 °C

2: 92 percent / NBS; NaHCO₃ / tetrahydrofuran / 2 h / -78 °C

3: 85 percent / dimethylformamide / 18 h / 23 °C

With N-Bromosuccinimide; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol026205p

upstream raw materials:

sodium benzenesulfonate

Carbonic acid (2E,6E)-9-(2-bromo-acetyl)-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

Carbonic acid (2E,6E)-9-acetyl-2,6,9,13-tetramethyl-12-methylene-tetradeca-2,6-dienyl ester methyl ester

Carbonic acid methyl ester (2E,6E)-2,6,9,13-tetramethyl-12-methylene-9-(1-trimethylsilanyloxy-vinyl)-tetradeca-2,6-dienyl ester

Downstream raw materials:

(4E,8E)-11-Benzenesulfonyl-2,5,9-trimethyl-2-(4-methyl-3-methylene-pentyl)-cycloundeca-4,8-dienone