p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

Base Information

Chemical Name:p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate
CAS No.:412313-15-6
Molecular Formula:C₂₃H₃₂N₂O₆S₂Si
Molecular Weight:524.734
Hs Code.:

Synonyms:p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

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Chemical Property of p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

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Technology Process of p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

There total 11 articles about p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-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: 42.0%

: 412313-21-4
p-nitrobenzyl 2-<4-<<<<2-(tert-butyldimethylsilyloxy)ethyl>thio>thiocarbonyl>thio>-3-ethyl-2-oxo-1-azetidinyl>-2-(triphenylphosphoranylidene)acetate

: 79760-08-0
5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethylsulfanyl]-thiazole-4-carboxylic acid 4-nitro-benzyl ester

: 412313-15-6
p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: With hydroquinone; In xylene; at 120 - 130 ℃; for 6.5h;
DOI:10.1248/cpb.29.1854

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 412313-15-6
p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 48 percent / imidazole / CH₂Cl₂ / Ambient temperature

2: 1.) sodium isopropoxide / 1.) 5 min, isopropanol, 0 deg C, 2.) THF, 0 deg C, 45 min

3: 92 percent / benzene / 2 h / Heating

4: 1.) thionyl chloride, 2,6-lutidine, 2.) 2,6-lutidine / 1.) THF, -5 deg C, 20 min, 2.) 70 deg C, 4.5 h

5: 42 percent / hydroquinone / xylene / 6.5 h / 120 - 130 °C

With 1H-imidazole; 2,6-dimethylpyridine; thionyl chloride; sodium isopropylate; hydroquinone; In dichloromethane; xylene; benzene;
DOI:10.1248/cpb.29.1854

Reference yield:

: 79759-95-8,125606-62-4,125606-68-0,137623-35-9,137623-36-0,138513-11-8
(3S*,4R*)-N-(tert-butyldimethylsilyl)-3-ethyl-4-(phenylthio)azetidin-2-one

: 412313-15-6
p-nitrobenzyl 3-<<2-(tert-butyldimethylsilyloxy)ethyl>thio>-6-ethyl-7-oxo-4-thia-1-azabicyclo-<3.2.0>hept-2-ene-2-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / ethyl acetate; acetic acid / 1 h / Ambient temperature

2: tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 1.5 h / 0 °C

3: 1.) sodium isopropoxide / 1.) 5 min, isopropanol, 0 deg C, 2.) THF, 0 deg C, 45 min

4: 92 percent / benzene / 2 h / Heating

5: 1.) thionyl chloride, 2,6-lutidine, 2.) 2,6-lutidine / 1.) THF, -5 deg C, 20 min, 2.) 70 deg C, 4.5 h

6: 42 percent / hydroquinone / xylene / 6.5 h / 120 - 130 °C

With 2,6-dimethylpyridine; thionyl chloride; tetrabutyl ammonium fluoride; sodium isopropylate; acetic acid; hydroquinone; In tetrahydrofuran; acetic acid; ethyl acetate; xylene; benzene;
DOI:10.1248/cpb.29.1854