(2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

Base Information

Chemical Name:(2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine
CAS No.:885217-73-2
Molecular Formula:C₂₂H₃₅NO₂S
Molecular Weight:377.591
Hs Code.:

Synonyms:(2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

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Chemical Property of (2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

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Technology Process of (2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

There total 5 articles about (2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine 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:

: 885217-66-3
(3R,7R,10S)-1-aza-3-benzyl-10-isopropyl-3-methyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone

: 75-03-6
ethyl iodide

: (2R,4S)-((2R)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

: 885217-73-2
(2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

Guidance literature:: (3R,7R,10S)-1-aza-3-benzyl-10-isopropyl-3-methyl-8-oxa-4-thiabicyclo[5.3.0]-2-decanone; With ammonia; lithium; In tetrahydrofuran; at -78 ℃; for 0.166667h;

ethyl iodide; In tetrahydrofuran; at -78 ℃; for 4h; Title compound not separated from byproducts;
DOI:10.1021/ol060106k

Reference yield:

: 885217-55-0
(2-[1,3]-dioxolan-2-yl-ethylsulfanyl)-acetic acid methyl ester

: 885217-73-2
(2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / n-butyllithium / tetrahydrofuran; hexane / 16 h / 23 °C

2.1: BF₃*Et₂O / CH₂Cl₂ / 120 h

3.1: LDA; lithium chloride / tetrahydrofuran; hexane / 0.25 h / 0 °C

3.2: 88 percent / tetrahydrofuran; hexane / 16 h / 0 °C

4.1: LDA; lithium chloride / tetrahydrofuran; hexane / 0.25 h / 0 °C

4.2: 95 percent / tetrahydrofuran; hexane / 16 h / 0 °C

5.1: lithium; liq. ammonia / tetrahydrofuran / 0.17 h / -78 °C

5.2: tetrahydrofuran / 4 h / -78 °C

With n-butyllithium; boron trifluoride diethyl etherate; ammonia; lithium; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol060106k

Reference yield:

: 885217-56-1
2-(2-[1,3]dioxolan-2-yl-ethylsulfanyl)-N-(1-hydroxymethyl-2-methyl-propyl)-acetamide

: 885217-73-2
(2R,4S)-((2S)-2-ethyl-2-methyl-2,3-dihydrocinnamoyl)-4-isopropyl-2-(3-thiapentyl)-oxazolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 120 h

2.1: LDA; lithium chloride / tetrahydrofuran; hexane / 0.25 h / 0 °C

2.2: 88 percent / tetrahydrofuran; hexane / 16 h / 0 °C

3.1: LDA; lithium chloride / tetrahydrofuran; hexane / 0.25 h / 0 °C

3.2: 95 percent / tetrahydrofuran; hexane / 16 h / 0 °C

4.1: lithium; liq. ammonia / tetrahydrofuran / 0.17 h / -78 °C

4.2: tetrahydrofuran / 4 h / -78 °C

With boron trifluoride diethyl etherate; ammonia; lithium; lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol060106k