ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

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Chemical Name:ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate
CAS No.:1041262-63-8
Molecular Formula:C₂₃H₂₁NO₄S
Molecular Weight:407.49
Hs Code.:

Synonyms:ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

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Chemical Property of ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

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Technology Process of ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

There total 4 articles about ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate 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%

: 1212-08-4
S-Phenyl benzenethiosulfonate

: 1041262-62-7
ethyl (1S,5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohex-3-enecarboxylate

: 1041262-63-8
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

Guidance literature:: ethyl (1S,5S)-5-(1,3-dioxoisoindolin-2-yl)cyclohex-3-enecarboxylate; With potassium hexamethylsilazane; In tetrahydrofuran; at -78 ℃; for 6h;

S-Phenyl benzenethiosulfonate; In tetrahydrofuran; at -78 - 20 ℃; Further stages.;
DOI:10.1002/anie.200800282

Reference yield:

: cis-ethyl 5-(tert-butoxycarbonyloxy)cyclohex-3-enecarboxylate

: 1041262-63-8
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / tetrahydrofuran / 0.25 h / 20 - 40 °C / Inert atmosphere

1.2: 20 h / 40 °C / Inert atmosphere

2.1: potassium hexamethylsilazane / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With bis(η3-allyl-μ-chloropalladium(II)); potassium hexamethylsilazane; caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In tetrahydrofuran;
DOI:10.1002/chem.201003454

Reference yield:

: (±)-ethyl 5-hydroxycyclohex-3-enecarboxylate

: 1041262-63-8
ethyl (5S)-5-(1,3-dioxoisoindolin-2-yl)-1-(phenylthio)cyclohex-3-enecarboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1-methyl-1H-imidazole / tetrachloromethane / 18 h / 20 °C / Inert atmosphere

2.1: bis(η3-allyl-μ-chloropalladium(II)); caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane / tetrahydrofuran / 0.25 h / 20 - 40 °C / Inert atmosphere

2.2: 20 h / 40 °C / Inert atmosphere

3.1: potassium hexamethylsilazane / tetrahydrofuran / 6 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With 1-methyl-1H-imidazole; bis(η3-allyl-μ-chloropalladium(II)); potassium hexamethylsilazane; caesium carbonate; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In tetrahydrofuran; tetrachloromethane;
DOI:10.1002/chem.201003454