(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

Base Information

Chemical Name:(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile
CAS No.:1280199-27-0
Molecular Formula:C₁₉H₁₂Cl₅NO₂
Molecular Weight:463.575
Hs Code.:

Synonyms:(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

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Chemical Property of (4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

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Technology Process of (4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

There total 3 articles about (4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile 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:

: 1280199-16-7
(E)-1,1,1-trichloro-4-(2,4-dichlorophenyl)but-3-en-2-one

: 614-16-4
Benzoylacetonitrile

: (4R,6R)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

: 1280199-27-0
(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

Guidance literature:: With (S)-1-(1-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; at -10 ℃; for 36h; optical yield given as %ee; enantioselective reaction;
DOI:10.1016/j.tet.2011.01.043

Reference yield:

: C₁₀H₇Cl₅O

: (4R,6R)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

: 1280199-27-0
(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

Guidance literature:: Multi-step reaction with 2 steps

1: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere

2: (S)-1-(1-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea / 5,5-dimethyl-1,3-cyclohexadiene / 36 h / -10 °C

With manganese(IV) oxide; (S)-1-(1-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; In 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; 2: Michael condensation;
DOI:10.1016/j.tet.2011.01.043

Reference yield:

: 70017-27-5
3-(2,4-Dichlorophenyl)propenal

: (4R,6R)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

: 1280199-27-0
(4S,6S)-4-(2,4-dichlorophenyl)-6-hydroxy-2-phenyl-6-(trichloromethyl)-5,6-di-hydro-4H-pyran-3-carbonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: potassium hydroxide / methanol; N,N-dimethyl-formamide / 2 h / 0 °C

2: manganese(IV) oxide / dichloromethane / 20 °C / Inert atmosphere

3: (S)-1-(1-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea / 5,5-dimethyl-1,3-cyclohexadiene / 36 h / -10 °C

With manganese(IV) oxide; (S)-1-(1-(4-(benzo[d][1,3]dioxol-5-ylmethyl)piperazin-1-yl)-3-phenylpropan-2-yl)-3-(3,5-bis(trifluoromethyl)phenyl)thiourea; potassium hydroxide; In methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; N,N-dimethyl-formamide; 3: Michael condensation;
DOI:10.1016/j.tet.2011.01.043