p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Base Information

Chemical Name:p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate
CAS No.:114409-16-4
Molecular Formula:C₁₄H₁₂BrNO₄S
Molecular Weight:370.224
Hs Code.:

Synonyms:p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Chemical Property of p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

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Technology Process of p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

There total 16 articles about p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-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:

: 114408-98-9
p-methoxybenzyl 2-<(3S,4R)-3-bromo-4-formylthio-2-oxoazetidin-1-yl>-2-oxoacetate

: 114409-16-4
p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: With phosphorous acid trimethyl ester; In toluene; at 50 ℃; for 1h; Yield given;
DOI:10.1039/P19940000179

Reference yield:

: 96572-55-3
p-methoxybenzyl-6-α-bromopenicillanate

: 114409-16-4
p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 1.5 h / 5 °C

2: toluene / Heating

3: toluene / Heating

4: Et₃N / toluene / 2 h / 5 °C

5: NaI, 4-N,N-dimethylaminopyridine, PPh₃ / acetonitrile / -20 deg C, 30 min then 5 deg C, 45 min

6: O₃ / ethyl acetate / 1 h / -78 °C

7: trimethyl phosphite / toluene / 30 h / 95 °C

With dmap; ozone; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; phosphorous acid trimethyl ester; In dichloromethane; ethyl acetate; toluene; acetonitrile;
DOI:10.1039/c39890000371

Reference yield:

: 114488-60-7
p-methoxybenzyl 6-bromopenicillanate-1-oxide

: 114409-16-4
p-methoxybenzyl (5R,6S)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: toluene / Heating

2: toluene / Heating

3: Et₃N / toluene / 2 h / 5 °C

4: NaI, 4-N,N-dimethylaminopyridine, PPh₃ / acetonitrile / -20 deg C, 30 min then 5 deg C, 45 min

5: O₃ / ethyl acetate / 1 h / -78 °C

6: trimethyl phosphite / toluene / 30 h / 95 °C

With dmap; ozone; triethylamine; triphenylphosphine; sodium iodide; phosphorous acid trimethyl ester; In ethyl acetate; toluene; acetonitrile;
DOI:10.1039/c39890000371