4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

Base Information

Chemical Name:4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile
CAS No.:946525-40-2
Molecular Formula:C₂₀H₂₀ClNO₅
Molecular Weight:389.835
Hs Code.:

Synonyms:4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

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Chemical Property of 4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

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Technology Process of 4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

There total 10 articles about 4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile 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:

: 946525-42-4
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-cyanobenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 946525-40-2
4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

Guidance literature:: With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20 ℃;
DOI:10.1016/j.bmcl.2011.06.032

Reference yield:

: 32469-28-6,55515-28-1,55515-29-2,32384-65-9
(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one

: 946525-40-2
4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 4 h

1.3: 16 h / 20 °C

2.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: water; boron trifluoride diethyl etherate; triethylsilane / acetonitrile / 22 h / 10 - 30 °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

With triethylsilane; dmap; n-butyllithium; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; water; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; pentane;

Reference yield:

: 1079083-63-8
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-hydroxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 946525-40-2
4-(2-chloro-5-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)benzyl)benzonitrile

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

With lithium hydroxide monohydrate; water; triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;