diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

Base Information

Chemical Name:diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate
CAS No.:1447736-56-2
Molecular Formula:C₂₆H₃₂O₁₀
Molecular Weight:504.534
Hs Code.:

Synonyms:diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

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Chemical Property of diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

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Technology Process of diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

There total 14 articles about diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate 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:

: 1447736-55-1
ethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-2-oxoacetate

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

: 1447736-56-2
diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

Guidance literature:: In dichloromethane; at 20 ℃; for 1h; diastereoselective reaction;
DOI:10.1016/j.tet.2013.05.125

Reference yield:

: 5390-04-5
pent-1-yn-5-ol

: 1447736-56-2
diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 - -20 °C / Inert atmosphere

2.2: 3 h / -78 °C / Inert atmosphere

3.1: mercury(II) oxide; sulfuric acid / acetone; water / 24 h

4.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C

5.1: dichloromethane / 1 h / 20 °C

With n-butyllithium; sulfuric acid; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; Dess-Martin periodane; mercury(II) oxide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; 4.1: |Dess-Martin Oxidation / 5.1: |Wittig Olefination;
DOI:10.1016/j.tet.2013.05.125

Reference yield:

: rac-(4S,5S)-ethyl 5-(acetoxymethyl)-5-(N-methoxy-N-methylcarbamoyl)-2,2-dimethyl-[1,3]-dioxolane-4-carboxylate

: 1447736-56-2
diethyl 2-{2-(acetoxymethyl)-5-[3-(4-methoxybenzyloxy)propyl]-3-oxo-2,3-dihydrofuran-2-yl}-(Z)-but-2-enedioate

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.17 h / -78 - -20 °C / Inert atmosphere

1.2: 3 h / -78 °C / Inert atmosphere

2.1: mercury(II) oxide; sulfuric acid / acetone; water / 24 h

3.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 2 h / 20 °C

4.1: dichloromethane / 1 h / 20 °C

With n-butyllithium; sulfuric acid; sodium hydrogencarbonate; Dess-Martin periodane; mercury(II) oxide; In tetrahydrofuran; hexane; dichloromethane; water; acetone; 3.1: |Dess-Martin Oxidation / 4.1: |Wittig Olefination;
DOI:10.1016/j.tet.2013.05.125