(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

Base Information

Chemical Name:(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile
CAS No.:793673-35-5
Molecular Formula:C₄₇H₅₇NO₄Si₂
Molecular Weight:756.145
Hs Code.:

(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

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Chemical Property of (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

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Technology Process of (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

There total 12 articles about (Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile 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:

: 142-83-6,4488-48-6
trans,trans-2,4-Hexadienal

: 793673-35-5
(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

Guidance literature:: Multi-step reaction with 13 steps

1.1: Et₃N; NaI / pentane; acetonitrile / Heating

2.1: Br₂ / dimethylformamide / 1.5 h / -55 - -30 °C

2.2: 41 percent / dimethylformamide / -55 - 20 °C

3.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

4.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

5.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

6.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

7.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

8.1: 72 percent / K₂CO₃ / methanol / 2 h / 0 °C

9.1: 97 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -75 - -70 °C

10.2: 90 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 0.83 h / -78 - -75 °C

11.1: 91 percent / NaBH₄; ethylelediamine; H₂ / Mi(OAc)2*4H₂O / ethanol / 1.5 h / 20 °C

12.1: 67 percent / aq. HCl / acetone / 2 h / 20 °C

13.1: 81 percent / imidasole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; dmap; sodium tetrahydroborate; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; hydrogen; bromine; potassium carbonate; ethylenediamine; triethylamine; sodium iodide; Mi(OAc)2*4H₂O; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile; tert-butyl alcohol; pentane; 5.1: Sharpless asymmetric epoxidation / 7.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o

Reference yield:

: 114434-56-9
1,(trimethylsilyloxy)hexa-1,3,5-triene

: 793673-35-5
(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

Guidance literature:: Multi-step reaction with 12 steps

1.1: Br₂ / dimethylformamide / 1.5 h / -55 - -30 °C

1.2: 41 percent / dimethylformamide / -55 - 20 °C

2.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

3.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

4.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

5.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

6.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

7.1: 72 percent / K₂CO₃ / methanol / 2 h / 0 °C

8.1: 97 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -75 - -70 °C

9.2: 90 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 0.83 h / -78 - -75 °C

10.1: 91 percent / NaBH₄; ethylelediamine; H₂ / Mi(OAc)2*4H₂O / ethanol / 1.5 h / 20 °C

11.1: 67 percent / aq. HCl / acetone / 2 h / 20 °C

12.1: 81 percent / imidasole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; dmap; sodium tetrahydroborate; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; hydrogen; bromine; potassium carbonate; ethylenediamine; sodium iodide; Mi(OAc)2*4H₂O; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 4.1: Sharpless asymmetric epoxidation / 6.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o

Reference yield:

: 793673-19-5
2-((1E,3E)-5-Bromo-penta-1,3-dienyl)-5,5-dimethyl-[1,3]dioxane

: 793673-35-5
(Z)-(R)-8-(tert-Butyl-diphenyl-silanyloxy)-8-[(2S,4S,5S)-4-(tert-butyl-diphenyl-silanyloxy)-5-((E)-3-oxo-propenyl)-tetrahydro-furan-2-yl]-oct-5-enenitrile

Guidance literature:: Multi-step reaction with 11 steps

1.1: 74 percent / K₂CO₃; NaI; CuI / acetone; heptane / 0.75 h / 20 °C

2.1: 61 percent / LiAlH₄ / diethyl ether / 6 h / 20 °C

3.1: 90 percent / Ti(OPr-i)4; diethyl L-tartrate / CH₂Cl₂ / 14.5 h / -30 - -20 °C

4.1: 96 percent / DMAP; Et₃M / CH₂Cl₂ / 3.5 h / 20 °C

5.1: 47 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 42 h / 0 °C

6.1: 72 percent / K₂CO₃ / methanol / 2 h / 0 °C

7.1: 97 percent / imidazole / CH₂Cl₂ / 12 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -75 - -70 °C

8.2: 90 percent / BF₃*OEt₂ / tetrahydrofuran; hexane / 0.83 h / -78 - -75 °C

9.1: 91 percent / NaBH₄; ethylelediamine; H₂ / Mi(OAc)2*4H₂O / ethanol / 1.5 h / 20 °C

10.1: 67 percent / aq. HCl / acetone / 2 h / 20 °C

11.1: 81 percent / imidasole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; hydrogenchloride; dmap; sodium tetrahydroborate; AD-mix-α; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; diethyl (2R,3R)-tartrate; methanesulfonamide; hydrogen; potassium carbonate; ethylenediamine; sodium iodide; Mi(OAc)2*4H₂O; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; water; acetone; tert-butyl alcohol; 3.1: Sharpless asymmetric epoxidation / 5.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo048863o