1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

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Chemical Name:1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime
CAS No.:1416164-49-2
Molecular Formula:C₂₃H₂₈ClNO₆
Molecular Weight:449.931
Hs Code.:

Synonyms:1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

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Chemical Property of 1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

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Technology Process of 1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

There total 12 articles about 1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime 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: 55.65%

: 1416165-14-4
1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone

: 3332-29-4
O-ethylhydroxylamine hydrochloride

: 1416164-49-2
1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

Guidance literature:: With potassium carbonate; In ethanol; at 0 - 20 ℃; for 1h; Inert atmosphere;

Reference yield:

: 1018898-77-5
(3aS,5R,6R,6aS)-6-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

: 1416164-49-2
1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 18 h / -78 - 20 °C

2.1: water; acetic acid / 22 h / 110 °C

2.2: 16 h / 20 °C

3.1: hydrogen bromide; acetic acid / 1 h / 20 °C

4.1: zinc(II) oxide / 1 h / 60 °C

5.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

6.1: N-ethyl-N,N-diisopropylamine / copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / N,N-dimethyl-formamide / 20 h / 100 °C / Inert atmosphere; Sealed vessel

7.1: formic acid / 2 h / 100 °C

8.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

9.1: potassium carbonate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

With n-butyllithium; formic acid; lithium hydroxide monohydrate; water; hydrogen bromide; potassium carbonate; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc(II) oxide; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 6.1: Sonogashira Coupling;

Reference yield:

: ((3aS,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(3-(4-((tert-butyldimethylsilyl)oxy)benzyl)-4-chlorophenyl)methanol

: 1416164-49-2
1-(4-(2-chloro-5-((2S,3R,4R,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)benzyl)phenyl)ethanone O-ethyl oxime

Guidance literature:: Multi-step reaction with 8 steps

1.1: water; acetic acid / 22 h / 110 °C

1.2: 16 h / 20 °C

2.1: hydrogen bromide; acetic acid / 1 h / 20 °C

3.1: zinc(II) oxide / 1 h / 60 °C

4.1: triethylamine / dichloromethane / 2 h / 0 - 20 °C

5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,1'-bis-(diphenylphosphino)ferrocene / N,N-dimethyl-formamide / 3 h / 150 °C

6.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 1 h / 0 - 20 °C

7.1: toluene; diethyl ether; tetrahydrofuran / 12 h / 90 °C

7.2: 20 °C

8.1: potassium carbonate / ethanol / 1 h / 0 - 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; water; hydrogen bromide; potassium carbonate; acetic acid; triethylamine; zinc(II) oxide; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;