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

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Chemical Name:(S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-4-phenyl-oxazolidin-2-one
CAS No.:201340-11-6
Molecular Formula:C₃₀H₄₃BrN₂O₄SSi
Molecular Weight:635.738
Hs Code.:

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

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

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

There total 12 articles about (S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-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: 77.0%

: 75-16-1
methylmagnesium bromide

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

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

: 201340-11-6
(S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-4-phenyl-oxazolidin-2-one

Guidance literature:: With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -20 ℃; Yields of byproduct given;
DOI:10.1021/ja973549f

Reference yield:

: 218782-66-2
(E)-(R)-5-Bromo-3-triisopropylsilanyloxy-hex-4-enethioic acid amide

: 201340-11-6
(S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-4-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

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

5: 1.) CuBr*DMS / 1.) THF, Et₂O, from -78 to 0 deg C, 30 min, 2.) THF, Et₂O, CH₂Cl₂, -30 deg C, 3.5 h

With 2,6-dimethylpyridine; copper(I) bromide dimethylsulfide complex; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; trifluoroacetic anhydride; In 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja981846u

Reference yield:

: 218782-63-9
(E)-(R)-5-Bromo-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-hex-4-en-1-one

: 201340-11-6
(S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-4-phenyl-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 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

8: 1.) CuBr*DMS / 1.) THF, Et₂O, from -78 to 0 deg C, 30 min, 2.) THF, Et₂O, CH₂Cl₂, -30 deg C, 3.5 h

With 2,6-dimethylpyridine; copper(I) bromide dimethylsulfide complex; (PhOPh)2P₂S₄; ammonia; sodium hexamethyldisilazane; diisobutylaluminium hydride; potassium hydrogencarbonate; trifluoroacetic anhydride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane;
DOI:10.1021/ja981846u