methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

Base Information

Chemical Name:methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate
CAS No.:1431956-36-3
Molecular Formula:C₂₈H₂₆O₁₁
Molecular Weight:538.508
Hs Code.:

Synonyms:methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

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Chemical Property of methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

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Technology Process of methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

There total 11 articles about methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate 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: 96.0%

: 1431956-35-2
methyl-3-(ethoxymethoxy)-4-(4-(3-(ethoxymethoxy)-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

: 1431956-36-3
methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

Guidance literature:: With silica gel supported sodium hydrogen sulfate; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1021/ol400864f

Reference yield:

: 23030-65-1
2-bromo-5-methoxycyclohexa-2,5-diene-1,4-dione

: 1431956-36-3
methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: benzene / 8 h / 20 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere

3.1: C₄H₁₂N⁽¹⁺⁾*C₂H₆I^(1-) / acetonitrile / 3 h / 25 - 68 °C

3.2: 4 h / 68 °C

4.1: caesium carbonate / acetone; N,N-dimethyl-formamide / 12 h / Reflux

5.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere

5.2: 4 h / 68 °C / Inert atmosphere

6.1: silica gel supported sodium hydrogen sulfate / dichloromethane / 4 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; silica gel supported sodium hydrogen sulfate; C₄H₁₂N⁽¹⁺⁾*C₂H₆I^(1-); potassium carbonate; caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene; 5.1: |Sonogashira Cross-Coupling / 5.2: |Sonogashira Cross-Coupling;
DOI:10.1021/ol400864f

Reference yield:

: 24308-01-8
5,7-dihydroxy-2-methoxynaphthalene-1,4-dione

: 1431956-36-3
methyl 3-hydroxy-4-(4-(3-hydroxy-1,6-dimethoxy-5,8-dioxo-5,8-dihydronaphthalen-2-yl)but-3-yn-1-yl)-2-methoxy-6-(2-methoxy-2-oxoethyl)benzoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere

2.1: C₄H₁₂N⁽¹⁺⁾*C₂H₆I^(1-) / acetonitrile / 3 h / 25 - 68 °C

2.2: 4 h / 68 °C

3.1: caesium carbonate / acetone; N,N-dimethyl-formamide / 12 h / Reflux

4.1: bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 1 h / 25 °C / Inert atmosphere

4.2: 4 h / 68 °C / Inert atmosphere

5.1: silica gel supported sodium hydrogen sulfate / dichloromethane / 4 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; silica gel supported sodium hydrogen sulfate; C₄H₁₂N⁽¹⁺⁾*C₂H₆I^(1-); potassium carbonate; caesium carbonate; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 4.1: |Sonogashira Cross-Coupling / 4.2: |Sonogashira Cross-Coupling;
DOI:10.1021/ol400864f