1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

Base Information

Chemical Name:1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime
CAS No.:1416164-45-8
Molecular Formula:C₂₄H₂₈ClNO₇
Molecular Weight:477.942
Hs Code.:

Synonyms:1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

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Chemical Property of 1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

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Technology Process of 1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

There total 15 articles about 1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl 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: 91.0%

: 1427286-32-5
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(4-(1-(methoxyimino)propyl)benzyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2.3,4-triyl triacetate

: 1416164-45-8
1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

Guidance literature:: With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 1h;

Reference yield:

: 864070-18-8
4-(5-bromo-2-chlorobenzyl)phenol

: 1416164-45-8
1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

Guidance literature:: Multi-step reaction with 15 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C

2.3: 16 h / 20 °C

3.1: leutidine / 12 h / 0 - 20 °C

4.1: collidine / dimethyl sulfoxide / 0.75 h / 150 °C

5.1: sodium ethanolate / ethanol / 20 h / 55 °C

5.2: 0.33 h

6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

7.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C

8.1: 1,3-dimethylbarbituric acid / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 90 °C

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

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

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

12.1: toluene; diethyl ether; tetrahydrofuran / 12 h / 80 °C

12.2: 20 °C

13.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 0 - 20 °C

14.1: sodium acetate; pyridine / ethanol / 5 h / Inert atmosphere; Reflux

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

With pyridine; dmap; n-butyllithium; 1,3-dimethylbarbituric acid; lithium hydroxide monohydrate; water; sodium ethanolate; sodium acetate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexanes; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

Reference yield:

: 1416165-16-6
2-(4-(allyloxy)benzyl)-4-bromo-1-chlorobenzene

: 1416164-45-8
1-(4-(2-chloro-5-((1S,2S,3S,4R,5S)-2,3,4-trihydroxy-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octan-5-yl)benzyl)phenyl)propan-1-one O-methyl oxime

Guidance literature:: Multi-step reaction with 14 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 °C

1.3: 16 h / 20 °C

2.1: leutidine / 12 h / 0 - 20 °C

3.1: collidine / dimethyl sulfoxide / 0.75 h / 150 °C

4.1: sodium ethanolate / ethanol / 20 h / 55 °C

4.2: 0.33 h

5.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

6.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: 1,3-dimethylbarbituric acid / tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 90 °C

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

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

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

11.1: toluene; diethyl ether; tetrahydrofuran / 12 h / 80 °C

11.2: 20 °C

12.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 0 - 20 °C

13.1: sodium acetate; pyridine / ethanol / 5 h / Inert atmosphere; Reflux

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

With pyridine; dmap; n-butyllithium; 1,3-dimethylbarbituric acid; lithium hydroxide monohydrate; water; sodium ethanolate; sodium acetate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexanes; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;