(5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

Base Information

Chemical Name:(5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one
CAS No.:790698-60-1
Molecular Formula:C₂₀H₂₇IO₄
Molecular Weight:458.336
Hs Code.:

Synonyms:(5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

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Chemical Property of (5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

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Technology Process of (5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

There total 6 articles about (5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one 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: 94.0%

: 488703-69-1
(2S)-N-methoxy-N-methyl-2-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-4-(4-methoxybenzyloxy)butanamide

: 1730-25-2
allylmagnesium bromide

: 790698-60-1
(5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

Guidance literature:: In tetrahydrofuran; diethyl ether; at -40 ℃; for 1h;
DOI:10.1021/ja0466863

Reference yield:

: t-butyldimethyl-{2-[(4S)-2-ethyl-5-oxo-1,3-dioxolan-4-yl]ethoxy}dimethylsilane

: 790698-60-1
(5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: TiCl₄ / CH₂Cl₂ / 3 h / -72 °C

1.2: 4.13 g / p-toluenesulfonic acid monohydrate / benzene / 1 h / Heating

2.1: 95 percent / N-iodosuccinimide; AgNO₃ / dimethylformamide / 0.17 h / 20 °C

3.1: 80 percent / potassium azodicarboxylate; AcOH / tetrahydrofuran; propan-2-ol / 6 h / 20 °C

4.1: AlEt₃ / CH₂Cl₂; toluene / 1 h / 0 - 20 °C

4.2: 93 percent / CH₂Cl₂; toluene / 0 - 20 °C

5.1: 82 percent / Ag₂O / CH₂Cl₂ / 24 h / 20 °C

6.1: 94 percent / tetrahydrofuran; diethyl ether / 1 h / -40 °C

With N-iodo-succinimide; triethylaluminum; potassium diazodicarboxylate; titanium tetrachloride; silver nitrate; acetic acid; silver(l) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;
DOI:10.1021/ja0466863

Reference yield:

: 488703-67-9
(3S)-{[(1S)-1-ethyl-3-iodopropynyl]oxy}tetrahydrofuran-2-one

: 790698-60-1
(5S)-5-{[(1S,2Z)-1-ethyl-3-iodo-2-propenyl]oxy}-7-(4-methoxybenzyloxy)-1-hepten-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 80 percent / potassium azodicarboxylate; AcOH / tetrahydrofuran; propan-2-ol / 6 h / 20 °C

2.1: AlEt₃ / CH₂Cl₂; toluene / 1 h / 0 - 20 °C

2.2: 93 percent / CH₂Cl₂; toluene / 0 - 20 °C

3.1: 82 percent / Ag₂O / CH₂Cl₂ / 24 h / 20 °C

4.1: 94 percent / tetrahydrofuran; diethyl ether / 1 h / -40 °C

With triethylaluminum; potassium diazodicarboxylate; acetic acid; silver(l) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; isopropyl alcohol; toluene;
DOI:10.1021/ja0466863