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

Base Information

Chemical Name:allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylate
CAS No.:138038-30-9
Molecular Formula:C₃₇H₅₅N₃O₇SSi₂
Molecular Weight:742.097
Hs Code.:

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

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Chemical Property of allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylate

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Technology Process of allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylate

There total 10 articles about allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-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: 83.0%

: 106-95-6
allyl bromide

: 159267-59-1
7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylic acid

: 138038-30-9
allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: With tetra(n-butyl)ammonium hydrogensulfate; sodium hydrogencarbonate; sodium iodide; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.7164/antibiotics.47.1052

Reference yield:

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

: 138038-30-9
allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1: 74 percent / LiCl / dichloropalladium(II) diacetonitrilate / dimethylformamide / 1 h / Ambient temperature

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

3: 91 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 1 h / Ambient temperature

4: 87 percent / 1.0M LiOH / tetrahydrofuran / 0.5 h / ultrasonic irradiation

5: 100 percent / H₂O, AcOH / acetonitrile / 2 h

6: 91 percent / propan-2-ol; 1,1,2-trichloro-ethane / 3 h / 65 °C

7: 320 mg / imidazole / dimethylformamide / 48 h

8: 82 percent / Zn, AcOH / dimethylformamide; tetrahydrofuran / 1.33 h

9: 83 percent / NaHCO₃, n-Bu₄N(+)*HSO₄(-), NaI / dimethylformamide / Ambient temperature

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

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 138038-30-9
allyl 7β-t-butoxycarbonylamino-1-carba(1-dethia)-3-<2-<3,4-di(t-butyldimethylsilyloxy)phenyl>thiazol-4-yl>-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

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

2: 87 percent / 1.0M LiOH / tetrahydrofuran / 0.5 h / ultrasonic irradiation

3: 100 percent / H₂O, AcOH / acetonitrile / 2 h

4: 91 percent / propan-2-ol; 1,1,2-trichloro-ethane / 3 h / 65 °C

5: 320 mg / imidazole / dimethylformamide / 48 h

6: 82 percent / Zn, AcOH / dimethylformamide; tetrahydrofuran / 1.33 h

7: 83 percent / NaHCO₃, n-Bu₄N(+)*HSO₄(-), NaI / dimethylformamide / Ambient temperature

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