(2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

Base Information

Chemical Name:(2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one
CAS No.:501644-61-7
Molecular Formula:C₁₉H₂₅NO₄S
Molecular Weight:363.478
Hs Code.:

Synonyms:(2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

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Chemical Property of (2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

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Technology Process of (2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

There total 3 articles about (2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-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: 61.0%

: 78-84-2
isobutyraldehyde

: 501644-55-9
(4S)-3-allyloxyacetyl-4-benzyl-1,3-oxazolidine-2-thione

: 501644-61-7
(2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

: (2S,3S)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

Guidance literature:: (4S)-3-allyloxyacetyl-4-benzyl-1,3-oxazolidine-2-thione; With titanium tetrachloride; (-)-sparteine; In dichloromethane; at -78 ℃; for 0.833333h;

isobutyraldehyde; With titanium tetrachloride; In dichloromethane; for 0.25h;
DOI:10.1021/ol034001i

Reference yield:

: 56680-79-6
allyloxyacetyl chloride

: 501644-61-7
(2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; various solvent(s) / 0.25 h / -78 °C

1.2: tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

2.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.83 h / -78 °C

2.2: 61 percent / TiCl₄ / CH₂Cl₂ / 0.25 h

With n-butyllithium; titanium tetrachloride; (-)-sparteine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol034001i

Reference yield:

: 22577-14-6
2-(allyloxy)acetic acid

: 501644-61-7
(2R,3R)-2-Allyloxy-1-((S)-4-benzyl-2-thioxo-oxazolidin-3-yl)-3-hydroxy-4-methyl-pentan-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 20 °C

2.1: n-butyllithium / tetrahydrofuran; various solvent(s) / 0.25 h / -78 °C

2.2: tetrahydrofuran; various solvent(s) / 1.5 h / 20 °C

3.1: TiCl₄; (-)-sparteine / CH₂Cl₂ / 0.83 h / -78 °C

3.2: 61 percent / TiCl₄ / CH₂Cl₂ / 0.25 h

With n-butyllithium; oxalyl dichloride; titanium tetrachloride; (-)-sparteine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ol034001i