2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

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Chemical Name:2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone
CAS No.:1357255-89-0
Molecular Formula:C₁₉H₁₉BrO₃
Molecular Weight:375.262
Hs Code.:

Synonyms:2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

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Chemical Property of 2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

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Technology Process of 2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

There total 4 articles about 2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone 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: 99.0%

: 1357255-87-8
(2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran

: 1357255-88-9
dimethyl 2-{4-[(tert-butyldimethylsilyl)oxy]phenyl}-2-oxoethylphosphonate

: 1357255-89-0
2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

Guidance literature:: (2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran; dimethyl 2-{4-[(tert-butyldimethylsilyl)oxy]phenyl}-2-oxoethylphosphonate; With lithium methanolate; In methanol; at 0 - 20 ℃; Inert atmosphere;

With ammonium chloride; In methanol; water; enantioselective reaction;
DOI:10.1002/anie.201106046

Reference yield:

: 1357255-86-7
5-(4-bromophenyl)-5-oxopentanal

: 1357255-89-0
2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

Guidance literature:: Multi-step reaction with 2 steps

1.1: trimethylsilyl trifluoromethanesulfonate; triphenylphosphine / dichloromethane / 1 h / 20 °C / Inert atmosphere

1.2: 6 h / -40 °C / Inert atmosphere

1.3: 2 h / 20 - 40 °C

2.1: lithium methanolate / methanol / 0 - 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; lithium methanolate; triphenylphosphine; In methanol; dichloromethane; 2.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201106046

Reference yield:

: 6725-74-2
1-bromo-4-(cyclopent-1-en-1-yl)benzene

: 1357255-89-0
2-[(2S,6R)-6-(4-bromophenyl)tetrahydro-2H-pyran-2-yl]-1-(4-hydroxyphenyl)ethanone

Guidance literature:: Multi-step reaction with 3 steps

1.1: ozone / dichloromethane / 1 h / -78 °C

1.2: -78 - 20 °C

2.1: trimethylsilyl trifluoromethanesulfonate; triphenylphosphine / dichloromethane / 1 h / 20 °C / Inert atmosphere

2.2: 6 h / -40 °C / Inert atmosphere

2.3: 2 h / 20 - 40 °C

3.1: lithium methanolate / methanol / 0 - 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; lithium methanolate; ozone; triphenylphosphine; In methanol; dichloromethane; 3.1: Horner-Wadsworth-Emmons olefination;
DOI:10.1002/anie.201106046