methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

Base Information

Chemical Name:methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate
CAS No.:1158845-36-3
Molecular Formula:C₁₄H₂₇N₂O₅P
Molecular Weight:334.353
Hs Code.:

Synonyms:methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

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Technology Process of methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

There total 7 articles about methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate 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: 43.0%

: methyl (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

: 1158845-36-3
methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

Guidance literature:: With trifluoroacetic acid; In water; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.ejmech.2016.05.016

Reference yield:

: dimethyl (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

: 1158845-36-3
methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide / water; 1,4-dioxane / 18 h / 20 °C / Inert atmosphere

1.2: Amberlite IR 120 hydrogen form / Inert atmosphere

2.1: trifluoroacetic acid / water / 1 h / 20 °C / Inert atmosphere

With trifluoroacetic acid; sodium hydroxide; In 1,4-dioxane; water;
DOI:10.1016/j.ejmech.2016.05.016

Reference yield:

: 204255-11-8
oseltamivir phosphate

: 1158845-36-3
methyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydrogencarbonate / water / 0.08 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide / water; 1,4-dioxane / 24 h / 20 °C / Inert atmosphere

3.2: Amberlite IR 120 hydrogen form / Inert atmosphere

4.1: triethylamine; S-(1-oxido-2-pyridyl)-thio-N,N,N',N'-tetramethyluronium hexafluorophosphate; dmap / tetrahydrofuran / 0.67 h / 20 °C / Darkness; Inert atmosphere

4.2: 1.5 h / Irradiation; Inert atmosphere

5.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; ethyl acetate / 1.5 h / 80 °C

6.1: sodium hydroxide / water; 1,4-dioxane / 18 h / 20 °C / Inert atmosphere

6.2: Amberlite IR 120 hydrogen form / Inert atmosphere

7.1: trifluoroacetic acid / water / 1 h / 20 °C / Inert atmosphere

With dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; triethylamine; trifluoroacetic acid; sodium hydroxide; S-(1-oxido-2-pyridyl)-thio-N,N,N',N'-tetramethyluronium hexafluorophosphate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; toluene;
DOI:10.1016/j.ejmech.2016.05.016