(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

Base Information

Chemical Name:(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one
CAS No.:952487-49-9
Molecular Formula:C₁₆H₂₁NO₂S₂
Molecular Weight:323.48
Hs Code.:

Synonyms:(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

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Chemical Property of (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

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Technology Process of (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

There total 8 articles about (2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-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: 91.0%

: 123-38-6
propionaldehyde

: 263764-23-4,863324-53-2
(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione

: 952487-49-9
(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

Guidance literature:: (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.333333h; Inert atmosphere;

With (-)-sparteine; In dichloromethane; at -78 - 0 ℃; for 0.383333h; Inert atmosphere;

propionaldehyde; In dichloromethane; at -78 - 0 ℃; diastereoselective reaction; Inert atmosphere;
DOI:10.15227/orgsyn.088.0364

Reference yield:

: 123-38-6
propionaldehyde

: 263764-23-4,863324-53-2
(S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione

: 952487-49-9
(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

: 1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

Guidance literature:: (S)-3-propanoyl-4-benzyl-1,3-thiazolidine-2-thione; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 1h;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.75h;

propionaldehyde; In dichloromethane; at -94 ℃; for 6.5h; Temperature; Overall yield = 88 percent; Overall yield = 250 g;

Reference yield:

: 3182-95-4
L-Phenylalaninol

: 952487-49-9
(2R,3S)-1-((S)-4-benzyl-2-thioxothiazolidin-3-yl)-3-hydroxy-2-methylpentan-1-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / dichloromethane / Inert atmosphere; Reflux

1.2: 1 h / Inert atmosphere; Reflux

2.1: carbon disulfide; potassium hydroxide / water / 16 h / 100 °C / Inert atmosphere; Reflux

3.1: triethylamine; dmap / dichloromethane / 3 h / 20 °C / Inert atmosphere

4.1: titanium tetrachloride / dichloromethane / 0.08 h / 0 °C / Inert atmosphere

4.2: 0.25 h / -78 - 0 °C / Inert atmosphere

4.3: 2 h / 0 °C / Inert atmosphere

With carbon disulfide; dmap; titanium tetrachloride; triethylamine; potassium hydroxide; In dichloromethane; water; 4.3: |Aldol Condensation;
DOI:10.1021/ol3023006