(S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

Base Information

Chemical Name:(S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one
CAS No.:1364681-07-1
Molecular Formula:C₂₄H₂₇NO₅
Molecular Weight:409.482
Hs Code.:

Synonyms:(S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

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Chemical Property of (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

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Technology Process of (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

There total 5 articles about (S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)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: 72.0%

: 1364680-56-7
(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one

: 135-02-4
ortho-anisaldehyde

: 1364681-07-1
(S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

Guidance literature:: ortho-anisaldehyde; With titanium tetrachloride; In dichloromethane; at -78 ℃; for 0.166667h; Inert atmosphere;

(S)-4-benzyl-3-((1E,3Z)-1-((tert-butyldimethylsilyl)oxy)-2-methylpenta-1,3-dien-1-yl)oxazolidin-2-one; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;
DOI:10.1021/ol300353w

Reference yield:

: (Z)-2-methylpent-3-enoic acid

: 1364681-07-1
(S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 16 h / 0 - 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

2.2: 1.25 h / -78 °C / Inert atmosphere

3.1: titanium tetrachloride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

With dmap; sodium hexamethyldisilazane; titanium tetrachloride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 3.2: Kobayashi aldol reaction;
DOI:10.1021/ol300353w

Reference yield:

: 1364680-50-1
(4S)-4-benzyl-3-((Z)-2-methylpent-3-enoyl)oxazolidin-2-one

: 1364681-07-1
(S)-4-benzyl-3-((4R,5R,E)-5-hydroxy-5-(2-methoxyphenyl)-2,4-dimethylpent-2-enoyl)oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 °C / Inert atmosphere

1.2: 1.25 h / -78 °C / Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

With sodium hexamethyldisilazane; titanium tetrachloride; In tetrahydrofuran; dichloromethane; 2.2: Kobayashi aldol reaction;
DOI:10.1021/ol300353w