tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

Base Information

Chemical Name:tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate
CAS No.:1333380-07-6
Molecular Formula:C₄₈H₅₄N₂O₁₀Si
Molecular Weight:847.05
Hs Code.:

tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

Synonyms:tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

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Chemical Property of tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

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Technology Process of tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

There total 6 articles about tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate 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: 87.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1333380-06-5
methyl (R,E)-2-(3-(benzo[d][1,3]dioxol-5-yl)acrylamido)-3-(5-((tert-butyldiphenylsilyl)-oxy)-1H-indol-3-yl)propanoate

: 1333380-07-6
tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

Guidance literature:: With dmap; triethylamine; In tetrahydrofuran; for 2.5h; Reflux;
DOI:10.1021/ol2021669

Reference yield:

: 93272-03-8
methyl (R)-3-(5-hydroxy-1H-indol-3-yl)-2-((methoxycarbonyl)amino)propanoate

: 1333380-07-6
tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / Inert atmosphere

2.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 2.5 h / Inert atmosphere; Reflux

2.2: 20 °C

2.3: pH > 7 / Saturated solution

3.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

4.1: dmap; triethylamine / tetrahydrofuran / 2.5 h / Reflux

With 1H-imidazole; dmap; chloro-trimethyl-silane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol2021669

Reference yield:

: 1333380-04-3
methyl (R)-3-(5-((tert-butyldiphenylsilyl)oxy)-1H-indol-3-yl)-2-((methoxycarbonyl)amino)propanoate

: 1333380-07-6
tert-butyl (R,E)-3-(2-(3-(benzo[d][1,3]dioxol-5-yl)-N-(tert-butoxycarbonyl)acrylamido)-3-methoxy-3-oxopropyl)-5-((tert-butyldiphenylsilyl)oxy)-1H-indole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: chloro-trimethyl-silane; sodium iodide / acetonitrile / 2.5 h / Inert atmosphere; Reflux

1.2: 20 °C

1.3: pH > 7 / Saturated solution

2.1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / tetrahydrofuran / 2.5 h / Reflux

With dmap; chloro-trimethyl-silane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium iodide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/ol2021669