(1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

Base Information

Chemical Name:(1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate
CAS No.:1352033-59-0
Molecular Formula:C₃₇H₃₈O₇
Molecular Weight:594.705
Hs Code.:

Synonyms:(1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

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Chemical Property of (1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

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Technology Process of (1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

There total 16 articles about (1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate 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: 92.0%

: 1352033-70-5
(E,5S)-1,7-di[4-(benzyloxy)-3-methoxyphenyl]-5-hydroxy-1-hepten-3-one

: 108-24-7
acetic anhydride

: 1352033-59-0
(1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.09.012

Reference yield:

: 100-39-0
benzyl bromide

: 1352033-59-0
(1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / 3 h / Inert atmosphere; Reflux

2.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / 0 °C / Inert atmosphere

2.2: 3 h / 0 °C / Inert atmosphere

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 50 °C / Inert atmosphere

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 °C

5.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; n-butyllithium; water; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; hexanes; dichloromethane; acetone; 2.2: Wittig reaction;
DOI:10.1016/j.tetasy.2011.09.012

Reference yield:

: 1352033-61-4
ethyl (E)-5-[4-(benzyloxy)-3-methoxyphenyl]-2-pentenoate

: 1352033-59-0
(1S,4E)-1-[4-(benzyloxy)-3-methoxyphenethyl]-5-[4-(benzyloxy)-3-methoxyphenyl]-3-oxo-4-pentenyl acetate

Guidance literature:: Multi-step reaction with 11 steps

1.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 0 °C / Inert atmosphere

1.2: Saturated solution

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 3 h / -24 °C / Molecular sieve; Inert atmosphere

3.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 0 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.2: 0 °C / Saturated solution

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 10 h / 20 °C / Cooling with ice; Inert atmosphere

7.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

7.2: Saturated solution

8.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dichloromethane; dimethyl sulfoxide / 12 h / 20 °C / Inert atmosphere; Cooling with ice

9.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 48 h / 50 °C / Inert atmosphere

10.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 0.5 h / 0 °C

11.1: dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; L-(+)-diisopropyl tartrate; water; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; toluene; 2.1: Sharpless epoxidation;
DOI:10.1016/j.tetasy.2011.09.012