4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

Base Information

Chemical Name:4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone
CAS No.:98303-29-8
Molecular Formula:C₂₂H₃₀N₂O₈Si
Molecular Weight:478.574
Hs Code.:

Synonyms:4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

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Chemical Property of 4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

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Technology Process of 4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

There total 6 articles about 4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone 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: 91.0%

: 98269-70-6
4-acetoxy-1-(tert-butyldimethylsilyl)-3-(2-hydroxy-1-methylethylidene)-2-azetidinone

: 4457-32-3
4-nitrobenzyl chloroformate

: 98303-29-8
4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

Guidance literature:: With dmap; In dichloromethane; at 0 ℃; for 0.75h;
DOI:10.1021/jo00222a012

Reference yield:

: 17458-90-1
3-methylbuta-1,2-dien-1-yl acetate

: 98303-29-8
4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 2.) Na₂SO₃, K₂HPO₄, H₂O / 1.) ether, -6 deg C to -2 deg C, 1.5 h, 2.)a) ether, 0 deg C, 30 min, b) RT, 1.5 h

2: 60 percent / triethylamine / dimethylformamide / 2 h / 0 °C

3: 1.5 g / NBS, AIBN / CCl₄ / 0.5 h / Heating

4: 90 percent / benzene / 1 h / Heating

5: 85 percent / aq. KHCO₃ / methanol / 0.5 h / Ambient temperature

6: 91 percent / (dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / 0 °C

With dmap; dipotassium hydrogenphosphate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; potassium hydrogencarbonate; triethylamine; sodium sulfite; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00222a012

Reference yield:

: 94492-87-2
4-acetoxy-3-(1-methylethylidene)-2-azetidinone

: 98303-29-8
4-acetoxy-1-(tert-butyldimethylsilyl)-3-<(E)-1-methyl-2-((((p-nitrobenzyl)oxy)carbonyl)oxy)ethylidene>-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 60 percent / triethylamine / dimethylformamide / 2 h / 0 °C

2: 1.5 g / NBS, AIBN / CCl₄ / 0.5 h / Heating

3: 90 percent / benzene / 1 h / Heating

4: 85 percent / aq. KHCO₃ / methanol / 0.5 h / Ambient temperature

5: 91 percent / (dimethylamino)pyridine / CH₂Cl₂ / 0.75 h / 0 °C

With dmap; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); potassium hydrogencarbonate; triethylamine; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jo00222a012