4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

Base Information

Chemical Name:4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate
CAS No.:86489-45-4
Molecular Formula:C₂₅H₂₃N₃O₁₁
Molecular Weight:541.471
Hs Code.:

Synonyms:4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

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Chemical Property of 4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

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Technology Process of 4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

There total 8 articles about 4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-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: 95.0%

: 86489-44-3
4-nitrobenzyl 2-diazo-4-{(2R,3S)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl]-4-oxoazetidine-2-yl}-3-oxobutanoate

: 86489-45-4
4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

Guidance literature:: With dirhodium tetraacetate; In diethyl ether; for 0.5h; Heating;
DOI:10.1016/S0040-4039(01)91123-2

Reference yield:

: 105995-50-4
magnesium 4-nitrobenzyl malonate

: 86489-45-4
4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / N,N'-carbonyldiimidazole / tetrahydrofuran / 17 h / Ambient temperature

2: p-TsN₃, Et₃N / acetonitrile / 0.5 h / 0 - 25 °C

3: 95 percent / Rh₂(OAc)4 / diethyl ether / 0.5 h / Heating

With dirhodium tetraacetate; 4-toluenesulfonyl azide; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; acetonitrile;
DOI:10.1016/S0040-4039(01)91123-2

Reference yield:

: 96124-69-5
2-[(R)-2-Allyl-3-(1-hydroxy-1-methyl-ethyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid methyl ester

: 86489-45-4
4-nitrobenzyl (2R,5R,6S)-3,7-dioxo-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-1-azabicyclo[3.2.0]-heptane-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N / CH₂Cl₂ / 48 h / Ambient temperature

2: 58.8 percent

3: 61 percent / n-BuLi / tetrahydrofuran / 2.5 h / -78 - 0 °C

4: 64 percent / KMnO₄, NaIO₄ / various solvent(s) / 17 h

5: 78 percent / N,N'-carbonyldiimidazole / tetrahydrofuran / 17 h / Ambient temperature

6: p-TsN₃, Et₃N / acetonitrile / 0.5 h / 0 - 25 °C

7: 95 percent / Rh₂(OAc)4 / diethyl ether / 0.5 h / Heating

With dirhodium tetraacetate; potassium permanganate; sodium periodate; n-butyllithium; 4-toluenesulfonyl azide; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(01)91123-2