(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

Base Information

Chemical Name:(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
CAS No.:667419-36-5
Molecular Formula:C₄₂H₇₀O₆Si₂
Molecular Weight:727.185
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 19 articles about (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 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: 58.0%

: 667419-44-5
(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

: 31930-36-6
ethyl (Z)-3-iodopropenoate

: 667419-36-5
(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

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:

: 667419-35-4
(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

: 667419-36-5
(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

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; bis(triphenylphosphine)palladium(II)-chloride; bromocyane; tri-n-butyl-tin hydride; In tetrahydrofuran; hexane; benzene;
DOI:10.1016/j.tet.2005.01.062

Reference yield:

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

: 667419-36-5
(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

Guidance literature:: Multi-step reaction with 7 steps

1.1: 100 percent / imidazole / dimethylformamide

2.1: 70 percent / ethylmagnesium bromide / tetrahydrofuran

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

4.1: aq. AcOH / tetrahydrofuran

5.1: Me₄NBH(OAc)3; AcOH / acetonitrile

6.1: 83 percent / PPTS / CH₂Cl₂

7.1: BrCN; n-BuLi / tetrahydrofuran / -78 - 40 °C

7.2: PdCl₂(PPh₃)2; Bu₃SnH / benzene

7.3: copper(I) 2-thiophenecarboxylate; NMP

With 1H-imidazole; n-butyllithium; bromocyane; 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