4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate

Base Information

• Chemical Name: 4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate
• CAS No.: 110312-12-4
• Molecular Formula: C₂₃H₃₂N₄O₇Si
• Molecular Weight: 504.615
• Mol file: 110312-12-4.mol

Synonyms:4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate

Chemical Property of 4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate

There total 1 articles about 4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate 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: 100.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester (90822-24-5) → 4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate (110312-12-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 5h; Ambient temperature;

DOI:10.1248/cpb.42.1381

Reference yield: 97.0%

trifluoromethylsulfonic anhydride (358-23-6) + 4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate (110312-12-4) → (4R,5R,6S)-4-nitrobenzyl-6-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-methyl-7-oxo-3-(((trifluoromethyl)sulfonyl)oxy)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:

4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate; With dirhodium tetraacetate; zinc(II) chloride; In dichloromethane; at 60 ℃; for 1h; Sealed tube; Inert atmosphere;

trifluoromethylsulfonic anhydride; With 2,2,6,6-tetramethyl-piperidine; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 1.08333h; Sealed tube; Cooling; Inert atmosphere;

DOI:10.1016/j.bioorg.2019.103405

Reference yield:

4-nitrobenzyl (R)-4-((2R,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-4-oxoazetidin-2-yl)-2-diazo-3-oxopentanoate (110312-12-4) → C23H32O7N2Si

Guidance literature:

With dirhodium tetraacetate; zinc(II) chloride; In dichloromethane; for 1.5h; Inert atmosphere; Reflux;

DOI:10.1002/anie.201612495

upstream raw materials:

tert-butyldimethylsilyl chloride

(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester