(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

Base Information

• Chemical Name: (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
• CAS No.: 667419-44-5
• Molecular Formula: C₃₇H₆₁BrO₄Si₂
• Molecular Weight: 705.964
• Mol file: 667419-44-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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:

(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) → (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 (667419-44-5)

Guidance literature:

With n-butyllithium; bromocyane; In tetrahydrofuran; hexane; at -78 - -40 ℃;

DOI:10.1016/j.tet.2005.01.062

Reference yield: 58.0%

(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 (667419-44-5) + ethyl (Z)-3-iodopropenoate (31930-36-6) → (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)

Guidance literature:

(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; With bis(triphenylphosphine)palladium(II)-chloride; tri-n-butyl-tin hydride; In benzene; at 20 ℃; for 0.5h;

ethyl (Z)-3-iodopropenoate; With copper(I) thiophene-2-carboxylate; at 0 ℃;

DOI:10.1016/j.tet.2005.01.062

Reference yield:

(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 (667419-44-5) → (2Z,4E)-(S)-7-{3-[(4R,6R)-6-((1E,3E)-(R)-8-Hydroxy-nona-1,3-dienyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-phenyl}-7-(1-methoxy-1-methyl-ethoxy)-hepta-2,4-dienoic acid

Guidance literature:

Multi-step reaction with 5 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

3.1: 82 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / 0 °C

4.1: 89 percent / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 24 h / 20 °C

5.1: KOH / tetrahydrofuran; ethanol / 2 h / 60 °C

With potassium hydroxide; bis(triphenylphosphine)palladium(II)-chloride; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; acetic acid; In tetrahydrofuran; ethanol; dichloromethane; benzene;

DOI:10.1016/j.tet.2005.01.062

upstream raw materials:

(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,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

(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

(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

(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