(1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

Base Information

Chemical Name:(1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane
CAS No.:1356563-90-0
Molecular Formula:C₂₂H₂₆O
Molecular Weight:306.448
Hs Code.:

Synonyms:(1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

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Chemical Property of (1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

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Technology Process of (1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

There total 5 articles about (1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane 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: 45.0%

: 1356563-86-4
1-{(R)-[(1R,2S,3R)-2-(benzyloxymethyl)-1-chloro-3-isopropyl-2-(2-phenylethyl)cyclopropyl]sulfinyl}-4-methylbenzene

: 1356563-90-0
(1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

Guidance literature:: 1-{(R)-[(1R,2S,3R)-2-(benzyloxymethyl)-1-chloro-3-isopropyl-2-(2-phenylethyl)cyclopropyl]sulfinyl}-4-methylbenzene; With isopropylmagnesium chloride; In tetrahydrofuran; at -78 - 0 ℃; for 2h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; water; Saturated solution;
DOI:10.1016/j.tet.2011.11.085

Reference yield:

: 123849-08-1
(-)-(R)-dichloromethyl p-tolyl sulfoxide

: 1356563-90-0
(1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / -85 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / Inert atmosphere

3.1: sodium hydride; sodium iodide / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

4.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / -78 - 0 °C / Inert atmosphere

4.2: Saturated solution

With sodium tetrahydroborate; isopropylmagnesium chloride; sodium hydride; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2011.11.085

Reference yield:

: 1312031-68-7
(1S,2R,3R)-ethyl 2-chloro-3-isopropyl-1-(2-phenylethyl)-2-((R)-p-tolylsulfinyl)cyclopropanecarboxylate

: 1356563-90-0
(1R,4R,5S,6S)-6-isopropyl-1-(2-phenylethyl)-4-phenyl-3-oxabicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate / Inert atmosphere

2.1: sodium hydride; sodium iodide / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / -78 - 0 °C / Inert atmosphere

3.2: Saturated solution

With sodium tetrahydroborate; isopropylmagnesium chloride; sodium hydride; sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2011.11.085