(-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate

Base Information

• Chemical Name: (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate
• CAS No.: 1237479-06-9
• Molecular Formula: C₂₅H₃₈N₄O₉SSi
• Molecular Weight: 598.75
• Mol file: 1237479-06-9.mol

Synonyms:(-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate

Chemical Property of (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate

There total 1 articles about (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate 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: 44.0%

tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-(1-hydroxybut-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate (1237479-21-8) + 4-nitrobenzenesulfonyl isocyanate (5769-16-4) → (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate + (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate (1237479-06-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.064

Reference yield: 76.0%

(-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((R)-1-((((4-nitrophenyl)sulfonyl)carbamoyl)oxy)but-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate (1237479-06-9) → (-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((4S,5S)-3-((4-nitrophenyl)sulfonyl)-2-oxo-4-vinyloxazolidin-5-yl)-4-oxoazetidin-3-yl)carbamate (1237479-08-1)

Guidance literature:

With (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride; [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate; 1,2-Bis(phenylsulfinyl)ethane; oxygen; 2-phenyl-1,4-benzoquinone; In tetrahydrofuran; at 45 ℃; for 24h; optical yield given as %de; diastereoselective reaction;

DOI:10.1016/j.tet.2010.04.064

upstream raw materials:

tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-(1-hydroxybut-3-en-1-yl)-4-oxoazetidin-3-yl)carbamate

4-nitrobenzenesulfonyl isocyanate

Downstream raw materials:

(-)-tert-butyl ((2R,3R)-1-(tert-butyldimethylsilyl)-2-((4S,5S)-3-((4-nitrophenyl)sulfonyl)-2-oxo-4-vinyloxazolidin-5-yl)-4-oxoazetidin-3-yl)carbamate