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

Base Information

Chemical Name:(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one
CAS No.:1297139-24-2
Molecular Formula:C₂₄H₂₅NO₄
Molecular Weight:391.467
Hs Code.:

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

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Chemical Property of (4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

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Technology Process of (4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

There total 6 articles about (4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one 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: 88.0%

: 14371-10-9
(E)-3-phenylpropenal

: 155399-10-3
(4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 1297139-24-2
(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

Guidance literature:: With chloro-trimethyl-silane; sodium hexafluoroantimonate; triethylamine; magnesium chloride; In ethyl acetate; at 20 ℃; for 17h;

Reference yield:

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

: 40217-17-2,90719-32-7,120574-96-1,102029-44-7
(R)-4-(phenylmethyl)-2-oxazolidinone

: 1297139-24-2
(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C

2.1: chloro-trimethyl-silane; triethylamine; sodium hexafluoroantimonate; magnesium chloride / ethyl acetate / 17 h / 20 °C

With n-butyllithium; chloro-trimethyl-silane; sodium hexafluoroantimonate; triethylamine; magnesium chloride; In tetrahydrofuran; hexane; ethyl acetate;

Reference yield:

: 14371-10-9
(E)-3-phenylpropenal

: 155399-10-3
(4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 1297139-24-2
(4R)-3-[(2S,3S,4E)-3-hydroxy-5-phenyl-2-(2-propen-1-yl)-4-pentenoyl]-4-(phenylmethyl)-1,3-oxazolidin-2-one

: (4R)-3-[(4E)-2-allyl-3-hydroxy-5-phenylpent-4-enoyl]-4-benzyl-1,3-oxazolidin-2-one

Guidance literature:: (E)-3-phenylpropenal; (4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one; With chloro-trimethyl-silane; sodium hexafluoroantimonate; triethylamine; magnesium chloride; In ethyl acetate; at 20 ℃; for 16h; Inert atmosphere;

With trifluoroacetic acid; In methanol; at 20 ℃; for 1h; Overall yield = 81 percent;
DOI:10.1021/acs.jmedchem.1c00374