N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide

Base Information

• Chemical Name: N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide
• CAS No.: 851487-22-4
• Molecular Formula: C₃₁H₃₄N₂O₆S
• Molecular Weight: 562.687
• Mol file: 851487-22-4.mol

Synonyms:N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide

Chemical Property of N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide

There total 3 articles about N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide 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: 93.0%

(2'R,4''R,2E)-4''-benzyl-3''-[3-(1'-tosylaziridin-2'-yl)acryloyl]-oxazolidin-2''-one (851487-20-2) + 3-phenyl-propionaldehyde (104-53-0) → N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide (851487-22-4)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1246/cl.2005.372 DOI:10.1246/bcsj.78.1309

Reference yield:

(2'R,2E)-3-(1'-tosylaziridin-2'-yl)acrylic methyl ester → N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide (851487-22-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LiOH / dioxane; methanol; H₂O / 4 h / 20 °C

2.1: pivaloyl chloride; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

2.2: 47 percent / LiCl / tetrahydrofuran / 0 - 20 °C

3.1: 93 percent / SmI₂ / tetrahydrofuran / 0.5 h / -78 °C

With lithium hydroxide; samarium diiodide; pivaloyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; water;

DOI:10.1246/bcsj.78.1309

Reference yield:

(2E)-3-[(2R)-1-tosylaziridin-2-yl]acrylic acid → N-[(E)-(4S,5R)-4-((R)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-hydroxy-7-phenyl-hept-2-enyl]-4-methyl-benzenesulfonamide (851487-22-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pivaloyl chloride; Et₃N / tetrahydrofuran / 0.75 h / 0 °C

1.2: 47 percent / LiCl / tetrahydrofuran / 0 - 20 °C

2.1: 93 percent / SmI₂ / tetrahydrofuran / 0.5 h / -78 °C

With samarium diiodide; pivaloyl chloride; triethylamine; In tetrahydrofuran;

DOI:10.1246/bcsj.78.1309

upstream raw materials:

(2'R,4''R,2E)-4''-benzyl-3''-[3-(1'-tosylaziridin-2'-yl)acryloyl]-oxazolidin-2''-one

3-phenyl-propionaldehyde

Downstream raw materials:

N-((E)-(4R,5R)-5-Hydroxy-4-hydroxymethyl-7-phenyl-hept-2-enyl)-4-methyl-benzenesulfonamide

(E)-(S)-2-((R)-1-Hydroxy-3-phenyl-propyl)-5-(toluene-4-sulfonylamino)-pent-3-enoic acid methyl ester