benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

Chemical Name:benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
CAS No.:115234-85-0
Molecular Formula:C₂₄H₂₄N₂O₅S
Molecular Weight:452.531
Hs Code.:

Synonyms:benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Chemical Property of benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

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Technology Process of benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 7 articles about benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-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%

: 115234-84-9
benzyl (2S,3R,5R,6R)-3-(1-acetyloxy-2-iodoethyl)-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 115234-85-0
benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: With acetic acid; zinc; In tetrahydrofuran; for 0.75h;
DOI:10.1016/S0040-4020(01)90038-9

Reference yield:

: 115252-98-7
benzyl (2S,3R,5R,6R)-3-hydroxymethyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 115234-85-0
benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / DMSO, oxalyl chloride, triethylamine / CH₂Cl₂ / -60 °C

2: ethyl acetate; diethyl ether / 1.) 0 deg C 5 h, 2.) room temp.12 h

3: trifluoroacetic anhydride, NaI / H₂O; acetonitrile / 1 h / Ambient temperature

4: 4-dimethylamino-pyridine / CH₂Cl₂ / 2.5 h

5: 100 percent / Zn, HOAc / tetrahydrofuran / 0.75 h

With dmap; oxalyl dichloride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; sodium iodide; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(01)90038-9

Reference yield:

: 115234-74-7
benzyl (2S,3R,5R,6R)-3-formyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 115234-85-0
benzyl (2S,3S,5R,6R)-3-ethenyl-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: ethyl acetate; diethyl ether / 1.) 0 deg C 5 h, 2.) room temp.12 h

2: trifluoroacetic anhydride, NaI / H₂O; acetonitrile / 1 h / Ambient temperature

3: 4-dimethylamino-pyridine / CH₂Cl₂ / 2.5 h

4: 100 percent / Zn, HOAc / tetrahydrofuran / 0.75 h

With dmap; acetic acid; trifluoroacetic anhydride; sodium iodide; zinc; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(01)90038-9