1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-

Base Information

• Chemical Name: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-
• CAS No.: 154428-43-0
• Molecular Formula: C18H17F3N2O9S
• Molecular Weight: 494.402
• Mol file: 154428-43-0.mol

Synonyms:

Chemical Property of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-, (4-nitrophenyl)methyl ester, (4R,5R,6S)-

There total 2 articles about 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-, (4-nitrophenyl)methyl ester, (4R,5R,6S)- 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:

trifluoromethylsulfonic anhydride (358-23-6) + p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate (90822-25-6) → (4R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (154428-43-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at -35 ℃;

DOI:10.1016/j.bmcl.2008.11.039

Reference yield:

trifluoromethylsulfonic anhydride (358-23-6) + 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate (104873-15-6) → (4R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (154428-43-0)

Guidance literature:

With triethylamine; at -78 ℃; for 0.5h;

DOI:10.1021/jo980381n

Reference yield: 39.0%

4-(4-nitrophenyl)-2-thiazolyl thiol (2104-10-1) + (4R,5R,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-7-oxo-3-trifluoromethanesulfonyloxy-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (154428-43-0) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[4-(4-nitro-phenyl)-thiazol-2-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:

With sodium hydride; In tetrahydrofuran; toluene; at 5 ℃; for 18h;

DOI:10.1016/S0968-0896(96)00273-8

upstream raw materials:

trifluoromethylsulfonic anhydride

4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate

p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate

Downstream raw materials:

4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate

(4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4S,5R,6S)-4-Methyl-7-oxo-3-(9-oxo-7-trimethylsilanyloxymethyl-9H-fluoren-3-yl)-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4S,5R,6S)-4-Methyl-7-oxo-3-[9-oxo-7-(propane-1-sulfonyloxymethyl)-9H-fluoren-3-yl]-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester