Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester

Base Information

• Chemical Name: Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester
• CAS No.: 911030-80-3
• Molecular Formula: C₂₂H₃₁NO₆S
• Molecular Weight: 437.557
• Mol file: 911030-80-3.mol

Synonyms:Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester

Chemical Property of Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester

There total 1 articles about Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester 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: 94.0%

benzenesulfonyl chloride (98-09-9) + (4S)-3-[(2E,4S,5R)-5-hydroxy-2,4,6-trimethylhept-2-enoyl]-4-isopropyloxazolidin-2-one (794525-14-7) → Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester (911030-80-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 - -40 ℃;

DOI:10.1016/j.tetlet.2006.06.158

Reference yield:

Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester (911030-80-3) → (E)-(R)-3-Hydroxy-2,4,6,8-tetramethyl-non-4-enoic acid (3-hydroxy-5-methoxy-phenyl)-amide (911030-83-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / LiBEt₃H / tetrahydrofuran / 12 h / -78 - 20 °C

2: 92 percent / MnO₂ / hexane / 12 h / 40 °C

3: 70 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

4: 96 percent / WSCI*HCl / CH₂Cl₂ / 2 h / 20 °C

With manganese(IV) oxide; lithium triethylborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.tetlet.2006.06.158

Reference yield:

Benzenesulfonic acid (E)-(1R,2S)-1-isopropyl-5-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,4-dimethyl-5-oxo-pent-3-enyl ester (911030-80-3) → (E)-(R)-2,4,6,8-Tetramethyl-3-oxo-non-4-enoic acid (3-methoxy-5,6-dioxo-cyclohexa-1,3-dienyl)-amide (911030-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 65 percent / LiBEt₃H / tetrahydrofuran / 12 h / -78 - 20 °C

2.1: 92 percent / MnO₂ / hexane / 12 h / 40 °C

3.1: 70 percent / LDA / tetrahydrofuran / 0.5 h / -78 °C

4.1: 96 percent / WSCI*HCl / CH₂Cl₂ / 2 h / 20 °C

5.1: o-iodoxybenzoic acid / toluene; dimethylsulfoxide / 0.5 h / 20 °C

5.2: 83 percent / toluene; dimethylsulfoxide / 12 h / 40 °C

With manganese(IV) oxide; lithium triethylborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; toluene; 5.1: Nicolaou oxidation;

DOI:10.1016/j.tetlet.2006.06.158

upstream raw materials:

benzenesulfonyl chloride

(4S)-3-[(2E,4S,5R)-5-hydroxy-2,4,6-trimethylhept-2-enoyl]-4-isopropyloxazolidin-2-one

Downstream raw materials:

(E)-(R)-3-Hydroxy-2,4,6,8-tetramethyl-non-4-enoic acid (3-hydroxy-5-methoxy-phenyl)-amide

(E)-(R)-2,4,6,8-Tetramethyl-3-oxo-non-4-enoic acid (3-methoxy-5,6-dioxo-cyclohexa-1,3-dienyl)-amide