benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Base Information

Chemical Name:benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate
CAS No.:214837-36-2
Molecular Formula:C₂₁H₂₉N₃O₄Si
Molecular Weight:415.564
Hs Code.:

Synonyms:benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

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Chemical Property of benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

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Technology Process of benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

There total 8 articles about benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<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:

: 145574-39-6
benzyl (1S,4S,5S)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

: 214837-36-2
benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / p-toluenesulfonic acid / dimethylformamide / 24 h

2: 88 percent / Et₃N / CH₂Cl₂ / 24 h

3: 65 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 50 °C

4: 1.) DMSO, (CF₃CO)2O, 2.) N-ethyldiisopropylamine / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

5: benzene / Heating

With pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm980023c

Reference yield:

: 145574-42-1
benzyl (1S,4S,5S)-6-(tert-butyldimethylsilanyl)-4-hydroxy-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

: 214837-36-2
benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) DMSO, (CF₃CO)2O, 2.) N-ethyldiisopropylamine / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

2: benzene / Heating

With dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In benzene;
DOI:10.1021/jm980023c

Reference yield:

: 214837-31-7
(1S,4S,5S)-2-(benzyloxycarbonyl)-4-(tetrahydropyran-2-yloxy)-2,6-diazabicyclo<3.2.0>heptan-7-one

: 214837-36-2
benzyl (1S,5R)-6-(tert-butyldimethylsilanyl)-4-(carbamoylmethylene)-7-oxo-2,6-diazabicyclo<3.2.0>heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / Et₃N / CH₂Cl₂ / 24 h

2: 65 percent / pyridinium p-toluenesulfonate / methanol / 24 h / 50 °C

3: 1.) DMSO, (CF₃CO)2O, 2.) N-ethyldiisopropylamine / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

4: benzene / Heating

With pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; In methanol; dichloromethane; benzene;
DOI:10.1021/jm980023c