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

Base Information

• Chemical Name: benzyl (-)-(6S,7S)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 182268-28-6
• Molecular Formula: C₁₅H₁₆N₂O₃S
• Molecular Weight: 304.37

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

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

Chemical Property:

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

There total 23 articles about benzyl (-)-(6S,7S)-7-amino-3-methyl-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: 100.0%

benzyl (-)-(6S,7S)-3-methyl-8-oxo-5-thia-7-(4-toluenesulfenamido)-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182186-48-7) → benzyl (-)-(6S,7S)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-28-6)

Guidance literature:

With sodium thiosulfate; acetic acid; potassium iodide; In methanol; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00486-5

Reference yield: 99.0%

benzyl (-)-(6S,7S)-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)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-28-6)

Guidance literature:

With sodium thiosulfate; acetic acid; potassium iodide; In methanol; at 0 ℃; for 2h;

DOI:10.1016/S0040-4020(00)00486-5

Reference yield: 47.0%

(6S,7S)-benzyl 7-(1,3-dioxoisoindolin-2-yl)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182186-35-2) → benzyl (-)-(6S,7S)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (182268-28-6)

Guidance literature:

With hydrazine hydrate; In N,N-dimethyl-formamide; at -15 ℃; for 0.5h;

DOI:10.1039/cc9960001989

upstream raw materials:

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

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

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

(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

Downstream raw materials:

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

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

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