(2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran

Base Information

Chemical Name:(2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran
CAS No.:1357255-87-8
Molecular Formula:C₁₁H₁₃BrO₂
Molecular Weight:257.127
Hs Code.:

Synonyms:(2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran

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Chemical Property of (2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran

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Technology Process of (2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran

There total 2 articles about (2RS,6R)-2-hydroxy-6-(4-bromophenyl)tetrahydropyran 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: 81.0%

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

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

Guidance literature:: 5-(4-bromophenyl)-5-oxopentanal; With trimethylsilyl trifluoromethanesulfonate; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; at -40 ℃; for 6h; Inert atmosphere;

With water; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; at 20 - 40 ℃; for 2h; enantioselective reaction;
DOI:10.1002/anie.201106046

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

With trimethylsilyl trifluoromethanesulfonate; ozone; triphenylphosphine; In dichloromethane;
DOI:10.1002/anie.201106046

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