p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

Chemical Name:p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
CAS No.:146142-33-8
Molecular Formula:C₂₆H₂₅N₃O₁₁
Molecular Weight:555.498
Hs Code.:

Synonyms:p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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Chemical Property of p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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Technology Process of p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 7 articles about p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-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: 34.0%

: 146039-58-9,146142-30-5,146142-31-6,146142-32-7,146142-34-9
p-nitrobenzyl (2R)- and (2S)-2-<(3S,4R)- and (3S,4S)-4-chloro-3-(p-nitrobenzyloxycarbonyloxymethyl)-2-oxoazetidin-1-yl>-4,4-dimethyl-3-oxopentanoates

: 146142-33-8
p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

: 146039-59-0
p-nitrobenzyl (+)-(5R,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: With potassium tert-butylate; In tetrahydrofuran; at -45 - -35 ℃; for 1h;
DOI:10.1055/s-1992-26329

Reference yield:

: 87154-05-0
(+)-(5R,7R,8S)-2,2,5-trimethyl-8-(1-p-nitrobenzyloxycarbonyloxymethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

: 146142-33-8
p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂ / 4.5 h / -5 - 5 °C

2: 75 percent / aq. AcOH / 2.5 h / Heating

3: 75 percent / acetonitrile; H₂O / 0.67 h / 0 °C

4: 70 percent / Cs₂CO₃ / acetonitrile / 4 h / 0 °C

5: 80 percent / lithium bisamide / tetrahydrofuran / 0.5 h / -75 °C

6: 92 percent / Cl₂ / CH₂Cl₂ / 0.67 h / -75 - -60 °C

7: KOBu-t / tetrahydrofuran / 1 h / -45 - -35 °C

With potassium tert-butylate; chlorine; caesium carbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1055/s-1992-26329

Reference yield:

: 87154-03-8
(+)-(3S,4R)-4-<(2R)-2-(1-hydroxypropyl)-sulfonyl>-3-(p-nitrobenzyloxycarbonyloxymethyl)azetidin-2-one

: 146142-33-8
p-nitrobenzyl (5S,6S)-3-tert-butyl-6-(p-nitrobenzyloxycarbonyloxymethyl)-7-oxo-4-oxa-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / acetonitrile; H₂O / 0.67 h / 0 °C

2: 70 percent / Cs₂CO₃ / acetonitrile / 4 h / 0 °C

3: 80 percent / lithium bisamide / tetrahydrofuran / 0.5 h / -75 °C

4: 92 percent / Cl₂ / CH₂Cl₂ / 0.67 h / -75 - -60 °C

5: KOBu-t / tetrahydrofuran / 1 h / -45 - -35 °C

With potassium tert-butylate; chlorine; caesium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1055/s-1992-26329