3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

Chemical Name:3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:84830-53-5
Molecular Formula:C₂₄H₃₁N₃O₇SSi
Molecular Weight:533.678
Hs Code.:

3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

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Chemical Property of 3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of 3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 10 articles about 3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester 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: 41.0%

: 10416-59-8
N,O-bis-(trimethylsilyl)-acetamide

: 84830-38-6
p-nitrobenzyl (5S^*,6S^*)-2-(2-acetamidoethyl)thio-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-1-em-3-carboxylate

: 84830-53-5
3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

: 109204-71-9
3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 2h; Ambient temperature;
DOI:10.1248/cpb.33.4346

Reference yield:

: 74819-64-0
(RS)-4-allyl-1-azetidin-2-one

: 84830-53-5
3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 51 percent / 1.) n-butyllithium, diisopropylamine; 2.) acetic acid / 1.) hexan/THF, -70 degC, 30 min; 2.) MeOH, room temperature

2: 95 percent / pyridine / toluene / 0.5 h

3: 96 percent / acetic acid, tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Ambient temperature

4: 1.) triethylamine; 2.) thionyl chloride, 2,6-lutidine / 1.) THF, room temperature; 2.) THF, -35 degC to -20 degC, 1.5 h

5: 2,6-lutidine / dioxane / Ambient temperature

6: 1.) ozone, trifluoroacetic acid, dimethylsulfide; 2.) NaHCO₃ / 1.) CH₂Cl₂, -60 degC, 1 h, room temperature; 2.) EtOAc/water, 1 h, room temperature

7: tetrahydrofuran; dimethylformamide / 1.5 h / Ambient temperature

8: m-chloroperbenzoic acid / CH₂Cl₂ / 30 h / ice-cooling

9: thionyl chloride, pyridine / 0.5 h / ice-cooling

10: 8 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; n-butyllithium; thionyl chloride; dimethylsulfide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.33.4346

Reference yield:

: 84829-82-3,84848-61-3,91926-19-1,91926-20-4
(3S^*,4R^*)-4-allyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone

: 84830-53-5
3-(2-Acetylamino-ethylsulfanyl)-6-[1-methyl-2-trimethylsilanyloxy-eth-(E)-ylidene]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) triethylamine; 2.) thionyl chloride, 2,6-lutidine / 1.) THF, room temperature; 2.) THF, -35 degC to -20 degC, 1.5 h

2: 2,6-lutidine / dioxane / Ambient temperature

3: 1.) ozone, trifluoroacetic acid, dimethylsulfide; 2.) NaHCO₃ / 1.) CH₂Cl₂, -60 degC, 1 h, room temperature; 2.) EtOAc/water, 1 h, room temperature

4: tetrahydrofuran; dimethylformamide / 1.5 h / Ambient temperature

5: m-chloroperbenzoic acid / CH₂Cl₂ / 30 h / ice-cooling

6: thionyl chloride, pyridine / 0.5 h / ice-cooling

7: 8 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / CH₂Cl₂ / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; thionyl chloride; dimethylsulfide; sodium hydrogencarbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1248/cpb.33.4346