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

Base Information

Chemical Name:benzyl (-)-(2S,4S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide
CAS No.:182268-33-3
Molecular Formula:C₂₃H₂₀N₂O₆S
Molecular Weight:452.488
Hs Code.:

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

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 5 articles about benzyl (-)-(2S,4S,5S,6R)-3,3-dimethyl-7-oxo-6-phthalimido-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate 4-oxide 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: 85.0%

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

: 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

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In chloroform; at 0 ℃; for 1.5h;
DOI:10.1016/S0040-4020(00)00486-5

Reference yield:

: 22509-74-6
N-ethoxycarbonylphthalimide

: 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

Guidance literature:: Multi-step reaction with 5 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

With chlorine; sodium carbonate; 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;
DOI:10.1016/S0040-4020(00)00486-5

Reference yield:

: 20425-27-8
(2S,5R,6R)-6-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

: 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

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / triethylamine / dimethylformamide / 6 h / 20 °C

2: Cl₂ / CH₂Cl₂; CCl₄ / 20 °C

3: 2.22 g / SnCl₂ / tetrahydrofuran / 2 h / 20 °C

4: 85 percent / m-chloroperbenzoic acid / CHCl₃ / 1.5 h / 0 °C

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