N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

Base Information

Chemical Name:N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide
CAS No.:1312944-79-8
Molecular Formula:C₂₆H₂₇FN₄O₇
Molecular Weight:526.521
Hs Code.:

Synonyms:N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

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Chemical Property of N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

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Technology Process of N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

There total 7 articles about N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide 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: 81.0%

: 1312944-70-9
N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[6-(4-fluorophenyl)-2,2-bis(4-methoxyphenyl)-1,3-benzodioxole-4-carboxamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

: 1312944-79-8
N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

Guidance literature:: With trifluoroacetic acid; In water; at 0 ℃; for 0.666667h; Inert atmosphere;
DOI:10.1002/chem.201003648

Reference yield:

: 6-bromo-2,2-bis-(4-methoxy-phenyl)-benzo[1,3]dioxole-4-carboxylic acid methyl ester

: 1312944-79-8
N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 3 h / 100 °C / Inert atmosphere

2.1: lithium hydroxide monohydrate / 70 °C / Inert atmosphere

3.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

3.2: 18 h / 0 °C / Inert atmosphere

4.1: trifluoroacetic acid / water / 0.67 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide monohydrate; potassium carbonate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In ethanol; water; N,N-dimethyl-formamide; toluene; 1.1: Suzuki coupling;
DOI:10.1002/chem.201003648

Reference yield:

: 303-38-8
2,3-Dihydroxybenzoic acid

: 1312944-79-8
N-ethyl-1-{(5E)-5,6,7-trideoxy-7-[5-(4-fluorophenyl)-2,3-dihydroxybenzamido]-β-D-ribo-hept-5-enofuranosyl}-1H-imidazole-4-carboxamide

Guidance literature:: Multi-step reaction with 7 steps

1.1: bromine; acetic acid / 20 h / 20 °C / Inert atmosphere

2.1: thionyl chloride / 15 h / 65 °C / Inert atmosphere

3.1: oxalyl dichloride / 3 h / 60 - 160 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate / ethanol; water; toluene / 3 h / 100 °C / Inert atmosphere

5.1: lithium hydroxide monohydrate / 70 °C / Inert atmosphere

6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 0 °C / Inert atmosphere

6.2: 18 h / 0 °C / Inert atmosphere

7.1: trifluoroacetic acid / water / 0.67 h / 0 °C / Inert atmosphere

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; oxalyl dichloride; lithium hydroxide monohydrate; bromine; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In ethanol; water; N,N-dimethyl-formamide; toluene; 4.1: Suzuki coupling;
DOI:10.1002/chem.201003648