p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate
CAS No.:230964-57-5
Molecular Formula:C₂₆H₃₂N₄O₇S
Molecular Weight:544.629
Hs Code.:

p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

Synonyms:p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

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Chemical Property of p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

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Technology Process of p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

There total 9 articles about p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-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: 60.5%

: 93711-81-0,90776-59-3,189188-38-3
(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 230964-56-4
(5S,7S)-2,2,3-trimethyl-7-mercapto-4-oxo-1,3-diazabicyclo<3.3.0>octane

: 230964-57-5
p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; for 2h;
DOI:10.1002/(SICI)1521-4184(19994)332:4<111::AID-ARDP111>3.0.CO;2-W

Reference yield:

: 96034-57-0
(2S,4R)-4-Hydroxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine-2-carboxylic acid

: 230964-57-5
p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: H₂SO₄ / 3 h / Heating

2: 97.1 percent / NEt₃ / CH₂Cl₂ / 1 h / 0 °C

3: 55.1 percent / aq. NH₃ / methanol / 10 h / Ambient temperature

4: H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 2585.74 Torr

5: Na₂SO₄ / 8 h / Heating

6: 89.1 percent / NaH / tetrahydrofuran / 24 h

7: 84.9 percent / dimethylformamide / 3 h / 65 °C

8: 89.1 percent / aq. NaOH / methanol / 0.33 h / 0 °C

9: 60.5 percent / iPr₂NEt / acetonitrile / 2 h / 0 °C

With ammonium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; sodium hydride; sodium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/(SICI)1521-4184(19994)332:4<111::AID-ARDP111>3.0.CO;2-W

Reference yield:

: 101803-29-6
(2S,4R)-4-hydroxy-2-methoxycarbonyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

: 230964-57-5
p-nitrobenzyl (1R,5S,6S)-6-<(1R)-1-hydroxyethyl>-2-<(5S,7S)-2,2,3-trimethyl-4-oxo-1,3-diazabicyclo<3.3.0>octan-7-ylthio>-1-methylcarbapen-2-em-3-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 97.1 percent / NEt₃ / CH₂Cl₂ / 1 h / 0 °C

2: 55.1 percent / aq. NH₃ / methanol / 10 h / Ambient temperature

3: H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 2585.74 Torr

4: Na₂SO₄ / 8 h / Heating

5: 89.1 percent / NaH / tetrahydrofuran / 24 h

6: 84.9 percent / dimethylformamide / 3 h / 65 °C

7: 89.1 percent / aq. NaOH / methanol / 0.33 h / 0 °C

8: 60.5 percent / iPr₂NEt / acetonitrile / 2 h / 0 °C

With ammonium hydroxide; sodium hydroxide; hydrogen; sodium hydride; sodium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/(SICI)1521-4184(19994)332:4<111::AID-ARDP111>3.0.CO;2-W