4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

Base Information

Chemical Name:4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid
CAS No.:1632161-89-7
Molecular Formula:C₂₉H₂₉NO₈
Molecular Weight:519.551
Hs Code.:

Synonyms:4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

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Chemical Property of 4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

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Technology Process of 4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

There total 3 articles about 4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid 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: 61.0%

: 1632161-88-6
ethyl4-[[6-[2-[bis(benzyloxycarbonyl)amino]ethynyl]-7-(4-ethoxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoate

: 1632161-89-7
4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

Guidance literature:: ethyl4-[[6-[2-[bis(benzyloxycarbonyl)amino]ethynyl]-7-(4-ethoxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoate; With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 5h;

With hydrogenchloride; In water;
DOI:10.1039/c4md00032c

Reference yield:

: 102653-36-1
3-bromonaphthalene-2,7-diol

: 1632161-89-7
4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

Guidance literature:: Multi-step reaction with 3 steps

1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C

2: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 15 h / 80 °C / Schlenk technique; Inert atmosphere

3: sodium hydroxide / methanol; tetrahydrofuran; water / 5 h / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; 2: |Sonogashira Cross-Coupling;
DOI:10.1039/c4md00032c

Reference yield:

: 582-17-2
2,7-Dihydroxynaphthalene

: 1632161-89-7
4-[[6-[2-(benzyloxycarbonylamino)ethynyl]-7-(4-hydroxy-4-oxo-butoxy)-2-naphthyl]oxy]butanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: bromine / acetic acid / 1.5 h

1.2: 24 h / 80 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 50 °C

3.1: triethylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide / N,N-dimethyl-formamide / 15 h / 80 °C / Schlenk technique; Inert atmosphere

4.1: sodium hydroxide / methanol; tetrahydrofuran; water / 5 h / 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bromine; potassium carbonate; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; water; acetic acid; N,N-dimethyl-formamide; 3.1: |Sonogashira Cross-Coupling;
DOI:10.1039/c4md00032c