4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

Base Information

Chemical Name:4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol
CAS No.:1414861-41-8
Molecular Formula:C₃₄H₄₄O₃Si
Molecular Weight:528.807
Hs Code.:

Synonyms:4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

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Chemical Property of 4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

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Technology Process of 4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

There total 16 articles about 4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol 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%

: 1414861-40-7
4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenyl pivalate

: 1414861-41-8
4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1055/s-0032-1316643

Reference yield:

: 1414861-31-6
5-iodo-2-(methoxymethoxy)-3-methylphenol

: 1414861-41-8
4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

Guidance literature:: Multi-step reaction with 11 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 19 h / 0 - 20 °C / Inert atmosphere

2.1: acetyl chloride / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

4.1: potassium carbonate; palladium diacetate / benzene / 24 h / Inert atmosphere; Reflux

5.1: (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; triethylamine / toluene / 22 h / -78 - 20 °C / Inert atmosphere

5.2: 0.5 h / 20 °C / Inert atmosphere

6.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

7.1: sodium tetrahydroborate; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

8.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

9.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

10.1: [Pd₂(dba)3]*CHCl₃; (R,R)-DACH-Ph / dichloromethane / 18 h / 20 °C / Inert atmosphere

11.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; di-isopropyl azodicarboxylate; potassium carbonate; [Pd₂(dba)3]*CHCl₃; (R,R)-DACH-Ph; water; palladium diacetate; boron tribromide; triethylamine; acetyl chloride; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene; 4.1: |Heck Reaction / 10.1: |Tsuji-Trost Allylation;
DOI:10.1055/s-0032-1316643

Reference yield:

: 1414861-32-7
(E)-1-(but-2-en-1-yloxy)-5-iodo-2-(methoxymethoxy)-3-methylbenzene

: 1414861-41-8
4-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methyl-6-((R,E)-pent-3-en-2-yloxy)phenol

Guidance literature:: Multi-step reaction with 10 steps

1.1: acetyl chloride / methanol; dichloromethane / 24 h / 20 °C / Inert atmosphere

2.1: dmap; triethylamine / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

3.1: potassium carbonate; palladium diacetate / benzene / 24 h / Inert atmosphere; Reflux

4.1: (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; triethylamine / toluene / 22 h / -78 - 20 °C / Inert atmosphere

4.2: 0.5 h / 20 °C / Inert atmosphere

5.1: triethylamine / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

6.1: sodium tetrahydroborate; water / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

7.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

8.1: boron tribromide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

9.1: [Pd₂(dba)3]*CHCl₃; (R,R)-DACH-Ph / dichloromethane / 18 h / 20 °C / Inert atmosphere

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; potassium carbonate; [Pd₂(dba)3]*CHCl₃; (R,R)-DACH-Ph; water; palladium diacetate; boron tribromide; triethylamine; acetyl chloride; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene; 3.1: |Heck Reaction / 9.1: |Tsuji-Trost Allylation;
DOI:10.1055/s-0032-1316643