p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

Base Information

Chemical Name:p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate
CAS No.:123289-24-7
Molecular Formula:C₂₇H₂₇N₃O₈
Molecular Weight:521.527
Hs Code.:

Synonyms:p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

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Chemical Property of p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

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Technology Process of p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

There total 2 articles about p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-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: 81.0%

: 97674-02-7
tributyl(1-ethoxyvinyl)stannane

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

: 123289-24-7
p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

Guidance literature:: With dichloro bis(acetonitrile) palladium(II); tetra-n-butyltin(IV); lithium chloride; In N,N-dimethyl-formamide; at 25 ℃;
DOI:10.1021/jo00285a037

Reference yield: 74.0%

: 108493-71-6
p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

: 112713-84-5
trimethyl(1-ethoxylvinyl)tin

: 123289-24-7
p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

Guidance literature:: With lithium chloride; dichloro bis(acetonitrile) palladium(II); In N,N-dimethyl-formamide; for 1h; Ambient temperature;
DOI:10.7164/antibiotics.47.1052

Reference yield:

: 123289-24-7
p-nitrobenzyl 7β-phenoxyacetylamido-1-carba(1-dethia)-3-(1-ethoxy-ethen-1-yl)-3-cephem-4-carboxylate

: allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<1,1-(3-pyridyl)(phenyl)methyl>thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.0M Br₂, 2,6-lutidine / CH₂Cl₂; CCl₄

2: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

3: 87 percent / 1.0M LiOH / tetrahydrofuran / 0.5 h / ultrasonic irradiation

4: 100 percent / H₂O, AcOH / acetonitrile / 2 h

5: 97 percent / propan-2-ol; 1,1,2-trichloro-ethane / 1 h / 65 °C

6: 1.) Zn, AcOH, 2.) NaHCO₃, n-Bu₄N(+)*HSO₄(-), NaI / 1.) DMF, THF, 2.) DMF, r.t.

With 2,6-dimethylpyridine; dmap; lithium hydroxide; water; bromine; tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; acetic acid; sodium iodide; zinc; In tetrahydrofuran; tetrachloromethane; dichloromethane; 1,1,2-trichloroethane; isopropyl alcohol; acetonitrile;
DOI:10.7164/antibiotics.47.1052