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

Base Information

Chemical Name:benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phthalimido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
CAS No.:182186-38-5
Molecular Formula:C₂₃H₁₈N₂O₅S
Molecular Weight:434.472
Hs Code.:

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

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

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

There total 6 articles about benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phthalimido-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: 33.0%

: 182268-33-3
benzyl (-)-(2S,4S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide

: 182186-38-5
benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phthalimido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 100 ℃; for 8h;
DOI:10.1039/cc9960001989

Reference yield:

: 59034-30-9
benzyl (-)-(2S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

: 182186-38-5
benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phthalimido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 85 percent / m-chloroperbenzoic acid / CHCl₃ / 1.5 h / 0 °C

2: 33 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 100 °C

With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In chloroform; N,N-dimethyl-formamide; 1: Oxidation / 2: Rearrangement;
DOI:10.1016/S0040-4020(00)00486-5

Reference yield:

: 22509-74-6
N-ethoxycarbonylphthalimide

: 182186-38-5
benzyl (-)-(6S,7R)-3-methyl-8-oxo-7-phthalimido-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 49 percent / Na₂CO₃ / H₂O / 2 h / 20 °C

2: 71 percent / triethylamine / dimethylformamide / 6 h / 20 °C

3: Cl₂ / CH₂Cl₂; CCl₄ / 20 °C

4: 2.22 g / SnCl₂ / tetrahydrofuran / 2 h / 20 °C

5: 85 percent / m-chloroperbenzoic acid / CHCl₃ / 1.5 h / 0 °C

6: 33 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 100 °C

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