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

Base Information

• Chemical Name: 3-((3R,4R)-5-((tert-Butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-6-methoxy-5-methyl-2-((R,E)-pent-3-en-2-yl)phenol
• CAS No.: 1414861-45-2
• Molecular Formula: C₃₅H₄₆O₃Si
• Molecular Weight: 542.834
• Mol file: 1414861-45-2.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about 3-((3R,4R)-5-((tert-Butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-6-methoxy-5-methyl-2-((R,E)-pent-3-en-2-yl)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:

tert-Butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane tert-Butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane tert-Butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane tert-butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane (1414861-42-9) → 3-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-6-methoxy-5-methyl-2-((S,E)-pent-3-en-2-yl)phenol (1414861-44-1) + 3-((3R,4R)-5-((tert-Butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-6-methoxy-5-methyl-2-((R,E)-pent-3-en-2-yl)phenol (1414861-45-2) + 5-((3R,4R)-5-((tert-butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-2-methoxy-3-methylphenol (1414861-43-0)

Guidance literature:

With tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); In toluene; at 120 ℃; for 22h; Inert atmosphere;

DOI:10.1055/s-0032-1316643

Reference yield:

(E)-2-(but-2-enyloxy)-4-iodo-6-methylphenyl pivalate (1414861-34-9) → 3-((3R,4R)-5-((tert-Butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-6-methoxy-5-methyl-2-((R,E)-pent-3-en-2-yl)phenol (1414861-45-2)

Guidance literature:

Multi-step reaction with 10 steps

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

2.1: (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

2.2: 0.5 h / 20 °C / Inert atmosphere

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

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

5.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

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

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

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

9.1: potassium carbonate / acetone / 96 h / 20 °C / Inert atmosphere

10.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / toluene / 22 h / 120 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); (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; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; acetone; toluene; benzene; 1.1: |Heck Reaction / 7.1: |Tsuji-Trost Allylation / 10.1: |Claisen Rearrangement;

DOI:10.1055/s-0032-1316643

Reference yield:

2-[(E)-but-2-en-1-yloxy]-6-methyl-4-[(E)-3-(propionyloxy)prop-1-en-1-yl]phenyl pivalate (1414861-35-0) → 3-((3R,4R)-5-((tert-Butyldiphenylsilyl)oxy)-4-methylpent-1-en-3-yl)-6-methoxy-5-methyl-2-((R,E)-pent-3-en-2-yl)phenol (1414861-45-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (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

1.2: 0.5 h / 20 °C / Inert atmosphere

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

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

4.1: 1H-imidazole; dmap / dichloromethane / 18 h / 20 °C / Inert atmosphere

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

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

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

8.1: potassium carbonate / acetone / 96 h / 20 °C / Inert atmosphere

9.1: tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) / toluene / 22 h / 120 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); (4S,5S)-1,3-bis[(3,5-bis(trifluoromethyl)phenyl)sulfonyl]-2-bromo-4,5-diphenyl-1,3,2-diazaborolidine; [Pd₂(dba)3]*CHCl₃; (R,R)-DACH-Ph; water; boron tribromide; potassium carbonate; triethylamine; In tetrahydrofuran; dichloromethane; acetone; toluene; 6.1: |Tsuji-Trost Allylation / 9.1: |Claisen Rearrangement;

DOI:10.1055/s-0032-1316643

upstream raw materials:

tert-Butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane tert-Butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane tert-Butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane tert-butyl[((2R,3R)-3-(4-methoxy-3-methyl-5-((R,E)-pent-3-en-2-yloxy)phenyl)-2-methylpent-4-en-1-yl)oxy]diphenylsilane

2-hydroxy-5-iodo-3-methylphenyl 4-methylbenzenesulfonate

5-iodo-2-(methoxymethoxy)-3-methylphenol

(E)-1-(but-2-en-1-yloxy)-5-iodo-2-(methoxymethoxy)-3-methylbenzene