1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

Base Information

Chemical Name:1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene
CAS No.:145362-84-1
Molecular Formula:C₃₀H₄₄O₄S
Molecular Weight:500.743
Hs Code.:

Synonyms:1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

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Chemical Property of 1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

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Technology Process of 1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

There total 7 articles about 1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene 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: 91.0%

: 24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7
farnesyl bromide

: 145362-83-0
6-(ethylenedioxy)-1-(benzenesulfonyl)-3-methyl-2(E)-hexene

: 145362-84-1
1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/0040-4020(95)00213-R

Reference yield: 90.0%

: 2-((E)-5-Benzenesulfonyl-3-methyl-pent-3-enyl)-[1,3]dioxolane

: 24163-93-7,24163-94-8,56881-57-3,6874-67-5,28290-41-7
farnesyl bromide

: 145362-84-1
1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

Guidance literature:: 2-((E)-5-Benzenesulfonyl-3-methyl-pent-3-enyl)-[1,3]dioxolane; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

farnesyl bromide; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1021/ja050340q

Reference yield:

: 37715-31-4
(E)-5-(3,3-dimethyloxiran-2-yl)-3-methylpent-2-enyl acetate

: 145362-84-1
1-(ethylenedioxy)-6-(benzenesulfonyl)-4,9,13,17-tetramethyl-4(E),8(E),12(E),16-octadecatetraene

Guidance literature:: Multi-step reaction with 6 steps

1: HIO₄*2H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 0 °C

2: p-TsOH / toluene / 5 h / Heating

3: 65 percent / K₂CO₃ / methanol / 10 h

4: 97 percent / N-chlorosuccinimide-DMS / CH₂Cl₂ / 6 h / 0 °C

5: 86 percent / dimethylformamide / 5 h / 0 °C

6: 1) n-BuLi / 1) THF, hexane, -78 deg C, 1.5 h, 2) THF, -78 deg C, 5 h

With n-butyllithium; potassium carbonate; toluene-4-sulfonic acid; N-chlorosuccinimide-dimethylsulfide complex; periodic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00052a043