(S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

Base Information

Chemical Name:(S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one
CAS No.:1403991-98-9
Molecular Formula:C₁₉H₂₅NO₄
Molecular Weight:331.412
Hs Code.:

Synonyms:(S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

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Chemical Property of (S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

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Technology Process of (S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

There total 4 articles about (S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-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: 91.0%

: (S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one

: 123-38-6
propionaldehyde

: 1403991-98-9
(S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

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

(S)-4-benzyl-3-{(1E,3E)-1[(tert-butyldimethylsilyl)oxy]-2-methylpenta-1,3-diene-1-yl}oxazolidin-2-one; In dichloromethane; at -78 ℃; for 20h; Optical yield = > 90.476 %de; Inert atmosphere;
DOI:10.1016/j.tet.2012.08.035

Reference yield:

: 16957-70-3
2-methylpent-2-enoic acid

: 1403991-98-9
(S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / 1 h / -78 - 20 °C / Cooling with acetone-dry ice

2.1: lithium chloride / dichloromethane / 21 h / -78 - 20 °C / Cooling with acetone-dry ice

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

3.2: 2.5 h / -78 °C

4.1: titanium tetrachloride / dichloromethane / 21 h / -78 - -40 °C

With titanium tetrachloride; triethylamine; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jacs.7b02875

Reference yield:

: C₁₁H₁₈O₃

: 1403991-98-9
(S)-3-((E,4S,5R)-5-hydroxyl-2,4-dimethylhept-2-enoyl)-4-benzyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: lithium chloride / dichloromethane / 21 h / -78 - 20 °C / Cooling with acetone-dry ice

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

2.2: 2.5 h / -78 °C

3.1: titanium tetrachloride / dichloromethane / 21 h / -78 - -40 °C

With titanium tetrachloride; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/jacs.7b02875