(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

Base Information

Chemical Name:(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid
CAS No.:1297139-01-5
Molecular Formula:C₁₄H₁₆O₃
Molecular Weight:232.279
Hs Code.:

Synonyms:(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

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Chemical Property of (2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

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Technology Process of (2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

There total 3 articles about (2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid 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: 79.0%

: 1297139-00-4
(4S)-3-[(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 1297139-01-5
(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

Guidance literature:: (4S)-3-[(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one; With lithium hydroxide monohydrate; dihydrogen peroxide; In tetrahydrofuran; water; at 0 - 20 ℃;

With hydrogenchloride; In water; pH=~ 2;

Reference yield:

: 104266-88-8
(4S)-4-benzyl-3-pent-4-enoyl-1,3-oxazolidin-2-one

: 1297139-01-5
(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: chloro-trimethyl-silane; triethylamine; sodium hexafluoroantimonate / magnesium chloride / ethyl acetate / 23 h / 20 °C

1.2: 0.5 h / 20 °C

2.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 20 °C

2.2: pH ~ 2

With chloro-trimethyl-silane; sodium hexafluoroantimonate; lithium hydroxide monohydrate; dihydrogen peroxide; triethylamine; magnesium chloride; In tetrahydrofuran; water; ethyl acetate;

Reference yield:

: 39716-58-0
pent-4-enoyl chloride

: 1297139-01-5
(2R,3R,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: chloro-trimethyl-silane; triethylamine; sodium hexafluoroantimonate / magnesium chloride / ethyl acetate / 23 h / 20 °C

2.2: 0.5 h / 20 °C

3.1: dihydrogen peroxide; lithium hydroxide monohydrate / water; tetrahydrofuran / 0 - 20 °C

3.2: pH ~ 2

With n-butyllithium; chloro-trimethyl-silane; sodium hexafluoroantimonate; lithium hydroxide monohydrate; dihydrogen peroxide; triethylamine; magnesium chloride; In tetrahydrofuran; hexane; water; ethyl acetate;