(+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate

Base Information

• Chemical Name: (+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate
• CAS No.: 790720-82-0
• Molecular Formula: C₂₀H₃₅NO₆Si
• Molecular Weight: 413.587

Synonyms:(+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate

Chemical Property of (+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate

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Technology Process of (+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate

There total 2 articles about (+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate 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: 72.0%

(+/-)-2-ethoxycarbonyl-3-(1-ethoxycarbonylcyclohex-3-ene)-propanate (790720-81-9) + 2-(Trimethylsilyl)ethanol (2916-68-9) → (+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate (790720-82-0)

Guidance literature:

(+/-)-2-ethoxycarbonyl-3-(1-ethoxycarbonylcyclohex-3-ene)-propanate; With TEA; diphenylphosphoranyl azide; In benzene; at 20 ℃; for 3h;

2-(Trimethylsilyl)ethanol; In benzene; for 12h; Heating;

DOI:10.1016/j.bmc.2004.06.037

Reference yield:

(+/-)-tert-butyl α,1-di(ethoxycarbonyl)-3-cyclohexenepropanoate (790720-80-8) → (+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate (790720-82-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4.33 g / TFA / 1,2-dimethoxy-ethane; 1,2-dichloro-ethane / 10 h

2.1: diphenylphosphorylazide; TEA / benzene / 3 h / 20 °C

2.2: 72 percent / benzene / 12 h / Heating

With TEA; diphenylphosphoranyl azide; trifluoroacetic acid; In 1,2-dimethoxyethane; 1,2-dichloro-ethane; benzene; 2.1: Curtius rearrangement;

DOI:10.1016/j.bmc.2004.06.037

Reference yield: 82.0%

(+/-)-ethyl 2-(N-2-trimethylsilylethoxycarbonyl)amino-3-(1-ethoxycarbonylcyclohex-3-ene)-propanoate (790720-82-0) + N-phenylselanylphthalimide (71098-88-9) → (+/-)-diethyl (1R,3RS,5S,7R)-2-(N-2-trimethylsilylethoxycarbonyl)-8-phenylselenyl-2-azabicyclo[3.3.1]nonane-3,5-dicarboxylate

Guidance literature:

With 10-camphorsufonic acid; In dichloromethane; for 12h; Heating;

DOI:10.1016/j.bmc.2004.06.037

upstream raw materials:

(+/-)-2-ethoxycarbonyl-3-(1-ethoxycarbonylcyclohex-3-ene)-propanate

2-(Trimethylsilyl)ethanol

(+/-)-tert-butyl α,1-di(ethoxycarbonyl)-3-cyclohexenepropanoate

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