2,4-Heptadienoic acid, 7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,3 -nonadienyl]-2,2-dimethyl-1,3-dioxan-4-yl]phenyl]-7-hydroxy-, ethyl ester, (2Z,4E,7S)-

Base Information

• Chemical Name: 2,4-Heptadienoic acid, 7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,3 -nonadienyl]-2,2-dimethyl-1,3-dioxan-4-yl]phenyl]-7-hydroxy-, ethyl ester, (2Z,4E,7S)-
• CAS No.: 667419-45-6
• Molecular Formula: C36H56O6Si
• Molecular Weight: 612.923
• Mol file: 667419-45-6.mol

Synonyms:

Chemical Property of 2,4-Heptadienoic acid, 7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,3 -nonadienyl]-2,2-dimethyl-1,3-dioxan-4-yl]phenyl]-7-hydroxy-, ethyl ester, (2Z,4E,7S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4-Heptadienoic acid, 7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,3 -nonadienyl]-2,2-dimethyl-1,3-dioxan-4-yl]phenyl]-7-hydroxy-, ethyl ester, (2Z,4E,7S)-

There total 21 articles about 2,4-Heptadienoic acid, 7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,3 -nonadienyl]-2,2-dimethyl-1,3-dioxan-4-yl]phenyl]-7-hydroxy-, ethyl ester, (2Z,4E,7S)- 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: 92.0%

(2Z,4E,7S)-7-tert-butyldimethylsilyloxy-7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)-nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxan-4-yl]]phenylhepta-2,4-dienoic acid ethyl ester (667419-36-5) → (2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-hydroxy-hepta-2,4-dienoic acid ethyl ester (667419-45-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2005.01.062

Reference yield:

ethyl (Z)-3-iodopropenoate (31930-36-6) → (2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-hydroxy-hepta-2,4-dienoic acid ethyl ester (667419-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bis(triphenylphosphine)palladium(II) chloride; tri-n-butyltin hydride / benzene / 0.5 h / 20 °C

1.2: 58 percent / copper(I) 2-thiophenecarboxylate / various solvent(s) / 0 °C

2.1: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With bis(triphenylphosphine)palladium(II)-chloride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; benzene;

DOI:10.1016/j.tet.2005.01.062

Reference yield:

(4R,6R)-4-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxane (667419-35-4) → (2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-hydroxy-hepta-2,4-dienoic acid ethyl ester (667419-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium; cyanogen bromide / tetrahydrofuran; hexane / -78 - -40 °C

2.1: bis(triphenylphosphine)palladium(II) chloride; tri-n-butyltin hydride / benzene / 0.5 h / 20 °C

2.2: 58 percent / copper(I) 2-thiophenecarboxylate / various solvent(s) / 0 °C

3.1: 92 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With n-butyllithium; bis(triphenylphosphine)palladium(II)-chloride; bromocyane; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; In tetrahydrofuran; hexane; benzene;

DOI:10.1016/j.tet.2005.01.062

upstream raw materials:

(2Z,4E,7S)-7-tert-butyldimethylsilyloxy-7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)-nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxan-4-yl]]phenylhepta-2,4-dienoic acid ethyl ester

(4R,6R)-4-{3-[(S)-4-Bromo-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-6-[(1E,3E)-(R)-8-(tert-butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxane

ethyl (Z)-3-iodopropenoate

(4R,6R)-4-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxane

Downstream raw materials:

(2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-(1-methoxy-1-methyl-ethoxy)-hepta-2,4-dienoic acid ethyl ester

(2Z,4E,7S)-7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-hydroxynona-1,3-dienyl]-2,2-dimethyl-1,3-dioxan-4-yl]]-phenyl-7-(1-methoxy-1-methylethoxy)hepta-2,4-dienoic acid ethyl ester