(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

Base Information

• Chemical Name: (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
• CAS No.: 667419-35-4
• Molecular Formula: C₃₇H₆₂O₄Si₂
• Molecular Weight: 627.068
• Mol file: 667419-35-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 17 articles about (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 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: 83.0%

2,2-dimethoxy-propane (77-76-9) + (4E,6E)-(1R,3R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-dodeca-4,6-diene-1,3-diol (667419-43-4) → (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)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1016/j.tetlet.2003.11.055

Reference yield: 74.0%

(4E,6E)-(1R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-dodeca-4,6-diene-1,3-diol + 2,2-dimethoxy-propane (77-76-9) → (4R,6S)-4-{3-[(S)-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 + (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)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2005.01.062

Reference yield:

(R)-(-)-8-Nonin-2-ol (156647-91-5) → (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)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / imidazole / dimethylformamide

2: 70 percent / ethylmagnesium bromide / tetrahydrofuran

3: bis(diphenylphosphino)butane / toluene; tetrahydrofuran / 20 °C

4: aq. AcOH / tetrahydrofuran

5: Me₄NBH(OAc)3; AcOH / acetonitrile

6: 83 percent / PPTS / CH₂Cl₂

With 1H-imidazole; bis(diphenylphosphino)butane; ethylmagnesium bromide; pyridinium p-toluenesulfonate; acetic acid; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1016/j.tetlet.2003.11.055

upstream raw materials:

2,2-dimethoxy-propane

(4E,6E)-(1R,3R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-dodeca-4,6-diene-1,3-diol

(R)-(-)-8-Nonin-2-ol

(R)-tert-butyldimethyl(non-8-yn-2-yloxy)silane

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)-(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)-(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,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