p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

Base Information

Chemical Name:p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate
CAS No.:84161-73-9
Molecular Formula:C₄₁H₃₆N₃O₉PS
Molecular Weight:777.791
Hs Code.:

Synonyms:p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

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Chemical Property of p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

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Technology Process of p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

There total 10 articles about p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate 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: 36.0%

: 117509-11-2,117604-07-6
p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)chloro acetate

: 603-35-0
triphenylphosphine

: 84161-73-9
p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

Guidance literature:: With 2,6-dimethylpyridine; In tetrahydrofuran; at 53 ℃; for 48h;
DOI:10.1139/v88-225

Reference yield:

: 41625-65-4
4-nitrobenzyl(2S,4S,5R,6R)-3,3-dimethyl-7-oxo-6-phenoxyacetamido-1-aza-4-thiabicyclo<3.2.0>heptane-2-carboxylate 4-oxide

: 84161-73-9
p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.)tert-butyl hypochlorite / 1.)CH₂Cl₂, -30 deg C, 2.)CH₂Cl₂, methanol, -30 deg C, 1 h

2: 1.)trimethyl phosphite 2.)triethylamine / 1.)toluene, 96 deg C, 24 h 2.)ethyl acetate, 3 h

3: 97 percent / ozone / CH₂Cl₂; methanol / -20 °C

4: B₂H₆ / tetrahydrofuran / 1 h / 0 - 5 °C

5: 34 percent / thionyl chloride, pyridine / tetrahydrofuran / 0.25 h / -27 °C

6: 36 percent / 2,6-lutidine / tetrahydrofuran / 48 h / 53 °C

With pyridine; 2,6-dimethylpyridine; thionyl chloride; tert-butylhypochlorite; ozone; triethylamine; diborane; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1139/v88-225

Reference yield:

: 41625-70-1
p-nitrobenzyl 6α-methoxy-6β-phenoxyacetamidopenicillanate-1β-oxide

: 84161-73-9
p-nitrobenzyl (4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)triphenylphosphoranylidene acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.)trimethyl phosphite 2.)triethylamine / 1.)toluene, 96 deg C, 24 h 2.)ethyl acetate, 3 h

2: 97 percent / ozone / CH₂Cl₂; methanol / -20 °C

3: B₂H₆ / tetrahydrofuran / 1 h / 0 - 5 °C

4: 34 percent / thionyl chloride, pyridine / tetrahydrofuran / 0.25 h / -27 °C

5: 36 percent / 2,6-lutidine / tetrahydrofuran / 48 h / 53 °C

With pyridine; 2,6-dimethylpyridine; thionyl chloride; ozone; triethylamine; diborane; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1139/v88-225