(S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one
• CAS No.: 218782-69-5
• Molecular Formula: C₂₉H₃₉BrN₂O₄SSi
• Molecular Weight: 619.695
• Mol file: 218782-69-5.mol

Synonyms:(S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

Chemical Property of (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one

There total 8 articles about (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-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:

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide (201339-99-3) → (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one (218782-69-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

2: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

3: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

4: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

5: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h

With 2,6-dimethylpyridine; (PhOPh)2P₂S₄; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja981846u

Reference yield:

(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one (218782-63-9) → (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one (218782-69-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.67 h / 0 - 20 °C

2: 90 percent / NH₃ gas / CH₂Cl₂ / 0 °C

3: 72 percent / (PhOPh)2P₂S₄ / tetrahydrofuran / 0.5 h / 25 °C

4: KHCO₃ / 1,2-dimethoxy-ethane / -30 - 25 °C

5: trifluoroacetic anhydride, 2,6-lutidine / 1,2-dimethoxy-ethane / 1 h / -30 °C

6: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

7: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h

With 2,6-dimethylpyridine; (PhOPh)2P₂S₄; ammonia; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja981846u

Reference yield:

2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carboxylic acid ethyl ester (201340-00-3) → (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one (218782-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / DIBAL-H / CH₂Cl₂ / 3 h / -90 °C

2: 1.) NaHMDS / 1.) THF, 25 deg C, 15 min, 2.) THF, 25 deg C, 1.5 h

With sodium hexamethyldisilazane; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/ja981846u

upstream raw materials:

2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazole-4-carbaldehyde

(4S)-3-[(diethylphosphoro)-acetyl]-4-phenyl-2-oxazolidinone

4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone

(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enoic acid amide

Downstream raw materials:

(S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-4-phenyl-oxazolidin-2-one

(R)-1-Benzyloxy-4-{(S)-2-[2-((E)-(R)-4-bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-propyl}-azetidin-2-one

(3S,5S)-5-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-3-hydroxy-hexanoic acid benzyloxy-amide

(-)-pateamine