3,8-Decadienoic acid, 4,8-dimethyl-2-[(4-methylphenyl)sulfonyl]-10-[(tetrahydro-2H-pyran-2-yl) oxy]-, (E,E)-

Base Information

• Chemical Name: 3,8-Decadienoic acid, 4,8-dimethyl-2-[(4-methylphenyl)sulfonyl]-10-[(tetrahydro-2H-pyran-2-yl) oxy]-, (E,E)-
• CAS No.: 111351-04-3
• Molecular Formula: C₂₄H₃₄O₆S
• Molecular Weight: 450.596
• Mol file: 111351-04-3.mol

Synonyms:

Chemical Property of 3,8-Decadienoic acid, 4,8-dimethyl-2-[(4-methylphenyl)sulfonyl]-10-[(tetrahydro-2H-pyran-2-yl) oxy]-, (E,E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,8-Decadienoic acid, 4,8-dimethyl-2-[(4-methylphenyl)sulfonyl]-10-[(tetrahydro-2H-pyran-2-yl) oxy]-, (E,E)-

There total 15 articles about 3,8-Decadienoic acid, 4,8-dimethyl-2-[(4-methylphenyl)sulfonyl]-10-[(tetrahydro-2H-pyran-2-yl) oxy]-, (E,E)- 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:

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3,8022-83-1) → (3E,8E)-4,8-Dimethyl-10-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyl)-deca-3,8-dienoic acid (111351-04-3)

Guidance literature:

Multi-step reaction with 15 steps

1: N-Methyl-morpholine N-oxide monohydrate, osmium tetraoxide / acetone; tetrahydrofuran; H₂O / 1). 18 h, room temperature, 2) 12 h, 50 deg C

2: Sodium periodate / dioxane; H₂O / 1.5 h / 0 - 5 °C

3: Lithium tri-tert-butoxyaluminium hydride / tetrahydrofuran / 0.17 h / Ambient temperature

4: 99 percent / pyridine / 3 h / 0 - 5 °C

5: 92 percent / Lithium bromide, sodium hydrogen carbonate / acetone / 72 h / Ambient temperature

6: 1.) Li, 2.) liq. NH₃ / 2.) Dimethyl sulfoxide, reflux, 2h; r. t., overnight

7: 99.5 percent / p-Toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

8: 1) 1.6 N n-Buthyllithium in hexane / 1) THF, 0-5 deg C, 40 min, 2) THF, -60 deg C to 0 deg C

9: 1) Sodium hydroxide / 1) CH₃OH, 2) room temperature, 2,5 h, CH₃OH

10: 1) Cuprous iodide / 1.) THF, -65 deg C, 30 min, 2.) THF

11: 95 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 5 °C

12: 1) 1.6 N n-Butyllithium in n-hexane, triphenylmethane / 1) Hexamethylphosphoric triamide, ether, 2) 0 deg C, 1 h

13: 23 g / Lithium bromide / hexamethylphosphoric acid triamide; diethyl ether; hexane / 12 h / Ambient temperature

14: 58 percent / dimethylformamide / 5 h / Ambient temperature

15: 1) 1.6 N n-Butyllitium in hexane / 1.) THF, -70 deg Cto -45 deg C to -95 deg C; 2.) 1,5 h; -95 deg C

With sodium hydroxide; sodium periodate; copper(l) iodide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; lithium tri(t-butoxy)aluminum hydride; triphenylmethane; ammonia; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; lithium bromide; In tetrahydrofuran; 1,4-dioxane; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

Reference yield:

(E)-6-acetoxy-4-methyl-4-hexenal (35334-60-2) → (3E,8E)-4,8-Dimethyl-10-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyl)-deca-3,8-dienoic acid (111351-04-3)

Guidance literature:

Multi-step reaction with 13 steps

1: Lithium tri-tert-butoxyaluminium hydride / tetrahydrofuran / 0.17 h / Ambient temperature

2: 99 percent / pyridine / 3 h / 0 - 5 °C

3: 92 percent / Lithium bromide, sodium hydrogen carbonate / acetone / 72 h / Ambient temperature

4: 1.) Li, 2.) liq. NH₃ / 2.) Dimethyl sulfoxide, reflux, 2h; r. t., overnight

5: 99.5 percent / p-Toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

6: 1) 1.6 N n-Buthyllithium in hexane / 1) THF, 0-5 deg C, 40 min, 2) THF, -60 deg C to 0 deg C

7: 1) Sodium hydroxide / 1) CH₃OH, 2) room temperature, 2,5 h, CH₃OH

8: 1) Cuprous iodide / 1.) THF, -65 deg C, 30 min, 2.) THF

9: 95 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 5 °C

10: 1) 1.6 N n-Butyllithium in n-hexane, triphenylmethane / 1) Hexamethylphosphoric triamide, ether, 2) 0 deg C, 1 h

11: 23 g / Lithium bromide / hexamethylphosphoric acid triamide; diethyl ether; hexane / 12 h / Ambient temperature

12: 58 percent / dimethylformamide / 5 h / Ambient temperature

13: 1) 1.6 N n-Butyllitium in hexane / 1.) THF, -70 deg Cto -45 deg C to -95 deg C; 2.) 1,5 h; -95 deg C

With sodium hydroxide; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; lithium tri(t-butoxy)aluminum hydride; triphenylmethane; ammonia; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium bromide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetone;

Reference yield:

essigsaeure-<(E)-6,7-dihydroxy-3,7-dimethyl-2-octenyl>ester (37715-33-6) → (3E,8E)-4,8-Dimethyl-10-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyl)-deca-3,8-dienoic acid (111351-04-3)

Guidance literature:

Multi-step reaction with 14 steps

1: Sodium periodate / dioxane; H₂O / 1.5 h / 0 - 5 °C

2: Lithium tri-tert-butoxyaluminium hydride / tetrahydrofuran / 0.17 h / Ambient temperature

3: 99 percent / pyridine / 3 h / 0 - 5 °C

4: 92 percent / Lithium bromide, sodium hydrogen carbonate / acetone / 72 h / Ambient temperature

5: 1.) Li, 2.) liq. NH₃ / 2.) Dimethyl sulfoxide, reflux, 2h; r. t., overnight

6: 99.5 percent / p-Toluenesulfonic acid / CH₂Cl₂ / 3 h / Ambient temperature

7: 1) 1.6 N n-Buthyllithium in hexane / 1) THF, 0-5 deg C, 40 min, 2) THF, -60 deg C to 0 deg C

8: 1) Sodium hydroxide / 1) CH₃OH, 2) room temperature, 2,5 h, CH₃OH

9: 1) Cuprous iodide / 1.) THF, -65 deg C, 30 min, 2.) THF

10: 95 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 5 °C

11: 1) 1.6 N n-Butyllithium in n-hexane, triphenylmethane / 1) Hexamethylphosphoric triamide, ether, 2) 0 deg C, 1 h

12: 23 g / Lithium bromide / hexamethylphosphoric acid triamide; diethyl ether; hexane / 12 h / Ambient temperature

13: 58 percent / dimethylformamide / 5 h / Ambient temperature

14: 1) 1.6 N n-Butyllitium in hexane / 1.) THF, -70 deg Cto -45 deg C to -95 deg C; 2.) 1,5 h; -95 deg C

With sodium hydroxide; sodium periodate; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; lithium tri(t-butoxy)aluminum hydride; triphenylmethane; ammonia; lithium; sodium hydrogencarbonate; toluene-4-sulfonic acid; lithium bromide; In tetrahydrofuran; 1,4-dioxane; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

upstream raw materials:

carbon dioxide

<(2E,7E)-3,7-Dimethyl-9-(tetrahydropyranyloxy)-2,7-nonadienyl>-p-Tolyl Sulfone

3,7-dimethyl-2E,6-octadien-1-yl acetate

(E)-6-acetoxy-4-methyl-4-hexenal

Downstream raw materials:

(1'R,2'R,6'R)-N-<(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetyl>-(S)-prolinol

(1'S,2'S,6'R)-N-<(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetyl>-(S)-prolinol

(1'R,2'R,6'S)-N-<(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetyl>-(S)-prolinol

(1'S,2'S,6'S)-N-<(2-Hydroxy-2,6-dimethyl-6-vinylcyclohexyl)acetyl>-(S)-prolinol

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