(S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal

Base Information

• Chemical Name: (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal
• CAS No.: 1554321-65-1
• Molecular Formula: C₃₂H₅₀O₅
• Molecular Weight: 514.746

Synonyms:(S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal

Chemical Property of (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal

There total 19 articles about (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal 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: 58.0%

(S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-en-1-ol (1554321-62-8) → (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal (1554321-65-1)

Guidance literature:

With manganese(IV) oxide; In chloroform; at 20 ℃; for 64h;

DOI:10.1021/ol500050p

Reference yield:

(R)-2-hydroxyheptyl p-toluenesulfonate (80800-66-4,120925-79-3) → (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal (1554321-65-1)

Guidance literature:

Multi-step reaction with 17 steps

1.1: sodium hydride / diethyl ether; mineral oil / 43 h / 0 - 20 °C / Inert atmosphere

2.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

3.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

4.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

4.2: 48 h / 20 °C / Inert atmosphere

5.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

6.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

7.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

8.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

8.2: 37 h / -78 - -20 °C

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.17 h / 0 - 20 °C

10.1: toluene-4-sulfonic acid / acetone / 13.5 h / 20 °C / Inert atmosphere

11.1: sodium; methanol / 19 h / 20 °C / Inert atmosphere

12.1: triethyl borane / toluene; hexane / 0.17 h / 20 °C / Inert atmosphere

12.2: air / 14 h / 20 °C

13.1: triethyl borane / dichloromethane / 2 h / -78 °C / Inert atmosphere

14.1: N-iodo-succinimide; 2,6-dimethylpyridine; hydroquinone / acetonitrile / 48 h / 0 - 20 °C / Inert atmosphere; Darkness

15.1: copper(l) iodide; cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 0 - 20 °C

17.1: manganese(IV) oxide / chloroform / 64 h / 20 °C

With 2,6-dimethylpyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; palladium diacetate; sodium; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; hydroquinone; triphenylphosphine; cesium fluoride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil; 15.1: |Stille Cross Coupling;

DOI:10.1021/ol500050p

Reference yield:

(R)-1,2-epoxyheptane (110549-07-0) → (S,E)-4-((4S,6R)-6-((R,E)-5-(4-methoxybenzyloxy)dec-2-en-2-yl)-2,2,5,5-tetramethyl-1,3-dioxan-4-yl)-2-methylpent-2-enal (1554321-65-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran / 151 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / dichloromethane / 143 h / 20 °C / Inert atmosphere

3.1: zinc trifluoromethanesulfonate; (-)-N-methylephedrine; triethylamine / tetrahydrofuran / 0.35 h / 20 °C / Inert atmosphere

3.2: 48 h / 20 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 2.5 h / -78 - -30 °C

5.1: diisobutylaluminium hydride / toluene; hexane / 1 h / -78 °C / Inert atmosphere

6.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-tetramethyl-piperidine-N-oxyl / dichloromethane / 74 h / 20 °C

7.1: palladium diacetate; triphenylphosphine / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

7.2: 37 h / -78 - -20 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.17 h / 0 - 20 °C

9.1: toluene-4-sulfonic acid / acetone / 13.5 h / 20 °C / Inert atmosphere

10.1: sodium; methanol / 19 h / 20 °C / Inert atmosphere

11.1: triethyl borane / toluene; hexane / 0.17 h / 20 °C / Inert atmosphere

11.2: air / 14 h / 20 °C

12.1: triethyl borane / dichloromethane / 2 h / -78 °C / Inert atmosphere

13.1: N-iodo-succinimide; 2,6-dimethylpyridine; hydroquinone / acetonitrile / 48 h / 0 - 20 °C / Inert atmosphere; Darkness

14.1: copper(l) iodide; cesium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide / 24 h / 60 °C / Inert atmosphere

15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 72 h / 0 - 20 °C

16.1: manganese(IV) oxide / chloroform / 64 h / 20 °C

With 2,6-dimethylpyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; manganese(IV) oxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-iodo-succinimide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethyl borane; [bis(acetoxy)iodo]benzene; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; palladium diacetate; sodium; pyridinium p-toluenesulfonate; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; hydroquinone; triphenylphosphine; cesium fluoride; In tetrahydrofuran; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 14.1: |Stille Cross Coupling;

DOI:10.1021/ol500050p

upstream raw materials:

(R)-2-hydroxyheptyl p-toluenesulfonate

(R)-1,2-epoxyheptane

(R)-(+)-non-1-yn-4-ol

1-Heptene

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