benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

Chemical Name:benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS No.:182186-39-6
Molecular Formula:C₂₁H₁₉N₃O₅S₂
Molecular Weight:457.531
Hs Code.:

Synonyms:benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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Technology Process of benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 11 articles about benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 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: 83.0%

: 937-32-6
4-nitrobenzenesulfenyl chloride

: 182268-34-4
benzyl (-)-(6S,7R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

: 182186-39-6
benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: With potassium carbonate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(00)00486-5

Reference yield: 52.0%

: 182186-44-3
benzyl (-)-(6S)-3-methyl-7-[[(4-methylphenyl)thio]imino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

: 182186-39-6
benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

: 182268-37-7
benzyl (-)-(6S,7S)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃; for 0.166667h; Title compound not separated from byproducts;
DOI:10.1039/cc9960001989

Reference yield:

: 59034-26-3
(2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

: 182186-39-6
benzyl (-)-(6S,7R)-3-methyl-7-(4-nitrobenzenesulfenamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: Cl₂ / CH₂Cl₂; CCl₄ / 20 °C

2: 2.22 g / SnCl₂ / tetrahydrofuran / 2 h / 20 °C

3: 85 percent / m-chloroperbenzoic acid / CHCl₃ / 1.5 h / 0 °C

4: 33 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 100 °C

5: 39 percent / N₂H₄*H₂O / dimethylformamide / 0.5 h / -15 °C

6: 83 percent / K₂CO₃ / CH₂Cl₂ / 1 h / 0 °C

With chlorine; potassium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; 3-chloro-benzenecarboperoxoic acid; tin(ll) chloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; chloroform; N,N-dimethyl-formamide; 1: Chlorination / 2: Cyclization / 3: Oxidation / 4: Rearrangement / 5: Substitution / 6: Substitution;
DOI:10.1016/S0040-4020(00)00486-5