4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

Chemical Name:4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
CAS No.:89063-96-7
Molecular Formula:C₂₃H₂₃N₃O₆S
Molecular Weight:469.518
Hs Code.:

Synonyms:4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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Chemical Property of 4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

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Technology Process of 4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 8 articles about 4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-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:

: 4556-23-4
pyridine-4-thiol

: 7087-68-5
N-ethyl-N,N-diisopropylamine

: 89063-94-5
4-nitrobenzyl (2R,5R,6R)-3,7-dioxo-6-(1-methoxy-1-methylethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

: 89063-96-7
4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: With dmap; trifluoromethanesulfonic acid anhydride; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

Reference yield:

: 86541-17-5
(6R)-2,2-dimethyl-3-oxa-1-azabicyclo<4.2.0>octan-8-one

: 89063-96-7
4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) n-BuLi, 3.) Ph₃SnH, 4.) HMPA

2: 95 percent / AcOH, H₂O / 0.5 h / 65 °C

3: 79 percent / Jones reagent / acetone / 40 h / Ambient temperature

4: 1.) N,N'-carbonyldiimidazole / 1.) THF, RT, 5 h, 2.) THF, RT, overnight

5: 1.) p-toluenesulfonyl azide, 2.) Et₃N / 1.) MeCN, 0 deg C, 10 min, 2.) MeCN, 0 deg C, 50 min

6: 100 percent / Rh₂(AcO)4 / benzene / 30 h / Heating

7: 1.) 4-(N,N-dimethylamino)pyridine, N,N-diisopropyl-N-ethylamine, (CF₃SO₂)2O, 2.) N,N-diisopropyl-N-ethylamine / 1.) CH₂Cl₂, -30 deg C, 30 min, 2.) CH₂Cl₂, DMF, a) -30 deg C, 30 min, b) 0 deg C, 30 min

With N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; dirhodium tetraacetate; n-butyllithium; 4-toluenesulfonyl azide; jones reagent; trifluoromethylsulfonic anhydride; triphenylstannane; water; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole; In acetone; benzene;

Reference yield:

: 89063-93-4
4-nitrobenzyl (2R,3R)-2-diazo-4-<3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl>-3-oxobutanoate

: 89063-96-7
4-nitrobenzyl (5R,6R)-6-(1-methoxy-1-methylethyl)-7-oxo-3-(4-pyridylthio)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / Rh₂(AcO)4 / benzene / 30 h / Heating

2: 1.) 4-(N,N-dimethylamino)pyridine, N,N-diisopropyl-N-ethylamine, (CF₃SO₂)2O, 2.) N,N-diisopropyl-N-ethylamine / 1.) CH₂Cl₂, -30 deg C, 30 min, 2.) CH₂Cl₂, DMF, a) -30 deg C, 30 min, b) 0 deg C, 30 min

With dmap; dirhodium tetraacetate; trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine; In benzene;