Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester
• CAS No.: 115094-15-0
• Molecular Formula: C₁₉H₂₈O₃S
• Molecular Weight: 336.496
• Mol file: 115094-15-0.mol

Synonyms:Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester

Chemical Property of Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester

There total 8 articles about Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl 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: 100.0%

(5E,7E)-(R)-4-Methyl-undeca-5,7-dien-1-ol (115094-14-9) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester (115094-15-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo00251a002

Reference yield:

(E)-2-Hexen-1-ol (928-95-0) → Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester (115094-15-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 100 percent / benzene / 10 h / Heating

2: 1.) n-BuLi / 1.) THF, hexane, RT, 45 min, 2.) RT, 3 h

3: pyridinium p-toluenesulfonate / ethanol / 4.5 h / 55 °C

4: 91.4 percent / trietylamine, 4-(dimethyloamino)pyridine / CH₂Cl₂ / 1.) 0 deg C, 3 h, 2.) RT, 5 h

5: 92 percent / sodium iodide / acetone / 20 h / 45 - 50 °C

6: 1.) dimsyl sodium / 1.) DMSO, 60 deg C, 1 h, 2.) 2 h

7: 100 percent / disodium hydrogen phosphate, sodium-mercury amalgam / methanol / 1 h / -5 °C

8: 97 percent / lithium aluminium hydride / tetrahydrofuran / 45 h / 0 °C

9: 100 percent / triethylamine, 4-(dimethyloamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; n-butyllithium; pyridinium p-toluenesulfonate; sodium methylsulfinylmethanide; triethylamine; sodium iodide; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; benzene;

DOI:10.1021/jo00251a002

Reference yield:

(R)-2-methyl-1-iodo-(E,E)-4,6-nonadiene (115094-10-5) → Toluene-4-sulfonic acid (5E,7E)-(R)-4-methyl-undeca-5,7-dienyl ester (115094-15-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) dimsyl sodium / 1.) DMSO, 60 deg C, 1 h, 2.) 2 h

2: 100 percent / disodium hydrogen phosphate, sodium-mercury amalgam / methanol / 1 h / -5 °C

3: 97 percent / lithium aluminium hydride / tetrahydrofuran / 45 h / 0 °C

4: 100 percent / triethylamine, 4-(dimethyloamino)pyridine / CH₂Cl₂ / 2 h / Ambient temperature

With dmap; disodium hydrogenphosphate; sodium amalgam; lithium aluminium tetrahydride; sodium methylsulfinylmethanide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00251a002

upstream raw materials:

(5E,7E)-(R)-4-Methyl-undeca-5,7-dien-1-ol

p-toluenesulfonyl chloride

(E)-2-Hexen-1-ol

(R)-2-methyl-1-iodo-(E,E)-4,6-nonadiene

Downstream raw materials:

(-)-8a-epipumiliotoxin c

(4-Bromo-phenyl)-((2R,4aS,5R)-5-methyl-2-propyl-4a,5,6,7,8,8a-hexahydro-2H-quinolin-1-yl)-methanone

(4-Bromo-phenyl)-((2S,4aR,5R)-5-methyl-2-propyl-4a,5,6,7,8,8a-hexahydro-2H-quinolin-1-yl)-methanone

Refernces