(2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

Base Information

Chemical Name:(2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol
CAS No.:1311260-46-4
Molecular Formula:C₁₃H₁₈O₂
Molecular Weight:206.285
Hs Code.:

Synonyms:

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Chemical Property of (2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

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Technology Process of (2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

There total 9 articles about (2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol 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:

: 98-86-2
acetophenone

: 1311260-46-4
(2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

: (2R,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / hexane / 0.5 h / 0 °C

1.2: Inert atmosphere; Reflux

2.1: diisobutylaluminium hydride / dichloromethane / 0 °C / Inert atmosphere

3.1: tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide / dichloromethane; water / 20 °C / Inert atmosphere

4.1: tris-(dibenzylideneacetone)dipalladium(0); (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; cesium fluoride / tetrahydrofuran; water / 36 h / 60 °C / Inert atmosphere

5.1: [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; bis(pinacol)diborane / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere

5.2: 4 h / 0 - 20 °C / Cooling with ice

5.3: 0 °C / Cooling with ice

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; tetra(n-butyl)ammonium hydrogensulfate; diisobutylaluminium hydride; cesium fluoride; bis(pinacol)diborane; sodium hydroxide; In tetrahydrofuran; hexane; dichloromethane; water;
DOI:10.1021/ja2039248

Reference yield:

: 1311260-02-2
tert-butyl (2-phenylbut-3-en-2-yl) carbonate

: 1311260-46-4
(2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

: (2R,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1.1: tris-(dibenzylideneacetone)dipalladium(0); (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; cesium fluoride / tetrahydrofuran; water / 12 h / 60 °C / Inert atmosphere

2.1: [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; bis(pinacol)diborane / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere

2.2: 4 h / 0 - 20 °C / Cooling with ice

2.3: 0 °C / Cooling with ice

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; cesium fluoride; bis(pinacol)diborane; In tetrahydrofuran; water;
DOI:10.1021/ja2039248

Reference yield:

: 6051-52-1
2-phenylbut-3-en-2-ol

: 1311260-46-4
(2S,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

: (2R,4S)-4-methyl-4-phenylhex-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere; Cooling with acetone-dry ice

1.2: -78 - 4 °C / Inert atmosphere

2.1: tris-(dibenzylideneacetone)dipalladium(0); (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; cesium fluoride / tetrahydrofuran; water / 12 h / 60 °C / Inert atmosphere

3.1: [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; bis(pinacol)diborane / tetrahydrofuran / 24 h / 60 °C / Inert atmosphere

3.2: 4 h / 0 - 20 °C / Cooling with ice

3.3: 0 °C / Cooling with ice

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; n-butyllithium; (R)-(+)-2,2′-bis(di-2-furanylphosphino)-6,6′-dimethoxy-1,1′-biphenyl; [Pt(1,5-diphenylpenta-1,4-dien-3-one)3]; cesium fluoride; bis(pinacol)diborane; In tetrahydrofuran; hexane; water;
DOI:10.1021/ja2039248