ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

Base Information

Chemical Name:ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate
CAS No.:292151-18-9
Molecular Formula:C₂₆H₃₀N₂O₃S
Molecular Weight:450.602
Hs Code.:

Synonyms:ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

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Chemical Property of ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

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Technology Process of ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

There total 12 articles about ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate 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: 95.0%

: 41302-32-3
ethyl 5-iodopentanoate

: 28092-52-6
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

: 292151-18-9
ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

Guidance literature:: ethyl 5-iodopentanoate; With chloro-trimethyl-silane; bromine; zinc; In tetrahydrofuran; toluene; at 50 - 60 ℃; for 1h;

(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione; With N,N-dimethyl-formamide; palladium on activated charcoal; In tetrahydrofuran; toluene; at 25 - 30 ℃; for 18h; Further stages.;
DOI:10.1002/adsc.200600610

Reference yield: 90.7%

: 109976-46-7
(5-ethoxy-5-oxopentyl)zinc(II) iodide

: 28092-52-6
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

: 292151-18-9
ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

Guidance literature:: (5-ethoxy-5-oxopentyl)zinc(II) iodide; (3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione; With palladium on activated charcoal; In toluene; at 30 ℃; for 15h;

With hydrogenchloride; In N,N-dimethyl-formamide; toluene; at 25 ℃; for 1h;

Reference yield:

: 28092-52-6
(3aS,6aR)-1,3-dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

: 292151-18-9
ethyl (3aS,4Z,6aR)-5-[1,3-dibenzyl-2,3,3a,4,6,6a-hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-5-ylidene]-pentanoate

Guidance literature:: Multi-step reaction with 2 steps

1: PdCl₂(PPh₃)2 / tetrahydrofuran; toluene; dimethylformamide / 35 h / 20 °C

2: 1.16 g / p-TsOH*H₂O / toluene / 18 h / 20 °C

With toluene-4-sulfonic acid; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 1: Alkylation / 2: Dehydration;
DOI:10.1016/S0040-4039(00)00781-4