(R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one

Base Information

• Chemical Name: (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one
• CAS No.: 1374979-90-4
• Molecular Formula: C₁₈H₂₅NO₂S₂
• Molecular Weight: 351.534
• Mol file: 1374979-90-4.mol

Synonyms:(R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one

Chemical Property of (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one

There total 4 articles about (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-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: 69.7%

1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone (911040-42-1) + hexanal (66-25-1) → (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one (1374979-90-4) + (S)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one (1374979-95-9)

Guidance literature:

1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

hexanal; In dichloromethane; at -78 ℃; for 0.5h; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tetasy.2012.03.002

Reference yield:

D-(R)-phenylalanine (673-06-3,25191-15-5,658-69-5,67675-33-6) → (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one (1374979-90-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium tetrahydroborate; iodine / tetrahydrofuran / 0 °C / Reflux

2.1: potassium hydroxide / water

3.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

4.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C

4.2: -78 °C

With dmap; sodium tetrahydroborate; iodine; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.tet.2014.05.107

Reference yield:

(R)-2-amino-3-phenylpropanol (5267-64-1) → (R)-1-((R)-4-benzyl-2-thioxo-thiazolidin-3-yl)-3-hydroxyoctan-1-one (1374979-90-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: potassium hydroxide / water

2.1: dmap; triethylamine / dichloromethane / 0 - 20 °C

3.1: titanium tetrachloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C

3.2: -78 °C

With dmap; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; potassium hydroxide; In dichloromethane; water;

DOI:10.1016/j.tet.2014.05.107

upstream raw materials:

1-[(4R)-4-benzyl-2-thioxo-1,3-thiazolidin-3-yl]ethanone

hexanal

(R)-4-benzyl-thiazolidine-2-thione

D-(R)-phenylalanine

Downstream raw materials:

2-((2R,4R,6R)-6-pentyl-2-phenyl-1,3-dioxan-4-yl)acetic acid

(2R,4S,6R)-4-allyl-6-pentyl-2-phenyl-1,3-dioxane

(R)-3-hydroxy-octanoic acid