4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

Base Information

Chemical Name:4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal
CAS No.:1578204-86-0
Molecular Formula:C₂₅H₂₄O₆
Molecular Weight:420.462
Hs Code.:

Synonyms:4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

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Chemical Property of 4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

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Technology Process of 4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

There total 6 articles about 4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal 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: 64.0%

: 1578204-83-7
4-(benzyloxy)-1-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)hept-2-yne-1,7-diol

: 1578204-86-0
4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

Guidance literature:: 4-(benzyloxy)-1-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)hept-2-yne-1,7-diol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.75h;

With triethylamine; In dichloromethane; at -78 - 20 ℃; for 1.5h;
DOI:10.1021/ol5002945

Reference yield:

: 5034-74-2
5-bromo-3-methoxysalicylaldehyde

: 1578204-86-0
4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

1.2: 0.5 h

2.1: toluene; tetrahydrofuran / 2 h

3.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.33 h / -78 °C

3.2: 1 h / -78 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 5 h / 20 °C

5.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / 48 h / 60 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

7.2: 1.5 h / -78 - 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; 7.1: |Swern Oxidation / 7.2: |Swern Oxidation;
DOI:10.1021/ol5002945

Reference yield:

: 1578204-71-3
1-(5-bromo-3-methoxy-2-(methoxymethoxy)phenyl)-1,7-bis(tert-butyldimethylsiloxy)hept-2-yn-4-ol

: 1578204-86-0
4-(benzyloxy)-7-(5-ethynyl-3-methoxy-2-(methoxymethoxy)phenyl)-7-oxohept-5-ynal

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 5 h / 20 °C

2.1: copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diisopropylamine / 48 h / 60 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

4.2: 1.5 h / -78 - 20 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; dimethyl sulfoxide; diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation;
DOI:10.1021/ol5002945