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

Base Information

Chemical Name:benzyl (2S,3S,5R,6R)-3-<(E)-2-cyanoethenyl>-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-azabicyclo<3.2.0>heptane-2-carboxylate
CAS No.:115234-76-9
Molecular Formula:C₂₅H₂₃N₃O₅S
Molecular Weight:477.541
Hs Code.:

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

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

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

There total 4 articles about benzyl (2S,3S,5R,6R)-3-<(E)-2-cyanoethenyl>-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-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: 79.0%

: 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

: 16640-68-9
cyanomethylene triphenylphosphorane

: 115234-76-9
benzyl (2S,3S,5R,6R)-3-<(E)-2-cyanoethenyl>-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: In benzene; at 60 ℃; 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

: 115234-76-9
benzyl (2S,3S,5R,6R)-3-<(E)-2-cyanoethenyl>-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

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

2: 79 percent / benzene / 0.75 h / 60 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)90038-9

Reference yield:

: 115234-72-5
benzyl (2S,3R,5R,6R)-3-chloroacetoxy-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 115234-76-9
benzyl (2S,3S,5R,6R)-3-<(E)-2-cyanoethenyl>-3-methyl-7-oxo-6-phenoxyacetamido-4-thia-azabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 53 percent / thiourea / ethanol / 1.) 70 deg C, 10 min, 2.) 50 deg C, 20 min

2: 100 percent / DMSO, oxalyl chloride, triethylamine / CH₂Cl₂ / -60 °C

3: 79 percent / benzene / 0.75 h / 60 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; thiourea; In ethanol; dichloromethane; benzene;
DOI:10.1016/S0040-4020(01)90038-9