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

Base Information

Chemical Name:methyl (R,E)-2-(3-(benzo[d][1,3]dioxol-5-yl)acrylamido)-3-(5-((tert-butyldiphenylsilyl)-oxy)-1H-indol-3-yl)propanoate
CAS No.:1333380-06-5
Molecular Formula:C₃₈H₃₈N₂O₆Si
Molecular Weight:646.815
Hs Code.:

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

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

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

There total 5 articles about methyl (R,E)-2-(3-(benzo[d][1,3]dioxol-5-yl)acrylamido)-3-(5-((tert-butyldiphenylsilyl)-oxy)-1H-indol-3-yl)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: 95.0%

: 1333380-05-4
methyl (R)-2-amino-3-(5-((tert-butyldiphenylsilyl)oxy)-1H-indol-3-yl)propanoate

: 2373-80-0,38489-76-8
3,4-methylenedioxy-trans-cinnamic acid

: 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

Guidance literature:: With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1021/ol2021669

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 3 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

With 1H-imidazole; dmap; chloro-trimethyl-silane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium iodide; In 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

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

Guidance literature:: Multi-step reaction with 2 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

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