[(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester

Base Information

• Chemical Name: [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester
• CAS No.: 84181-47-5
• Molecular Formula: C₃₅H₃₃N₂O₇PS
• Molecular Weight: 656.696

Synonyms:[(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester

Chemical Property of [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester

Chemical Property:

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Technology Process of [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester

There total 4 articles about [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester 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:

methyl 6-phenoxyacetamidopenicillanate-1β-oxide (24652-74-2) → [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (84181-47-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) tBuOCl / 1) THF, MeOH, -75 deg C, 2) THF, MeOH, 15 min, -70 deg C, than 20 min, -50 deg C

2: 1) triethyl phosphite, 2) Et₃N / 1) toluene, 4 h, 2) ethyl acetate

3: 1) O₃, 2) Zn / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, HOAc, -70 deg C to r.t.

4: 1) 2,4-lutidine, SOCl₂, 2) silica gel / 1) THF, -30 deg C to 0 deg C, 2) THF, 15 h

With thionyl chloride; 2,4-lutidine; tert-butylhypochlorite; silica gel; ozone; triethylamine; zinc; triethyl phosphite;

DOI:10.1039/c39820000933

Reference yield:

methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate (84161-62-6) → [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (84181-47-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) O₃, 2) Zn / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, HOAc, -70 deg C to r.t.

2: 1) 2,4-lutidine, SOCl₂, 2) silica gel / 1) THF, -30 deg C to 0 deg C, 2) THF, 15 h

With thionyl chloride; 2,4-lutidine; silica gel; ozone; zinc;

DOI:10.1039/c39820000933

Reference yield:

methyl 6α-methoxy-6β-phenoxyacetamidopenicillanate-1β-oxide (41625-69-8) → [(2R,3S)-2-Acetylsulfanyl-3-methoxy-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (84181-47-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) triethyl phosphite, 2) Et₃N / 1) toluene, 4 h, 2) ethyl acetate

2: 1) O₃, 2) Zn / 1) CH₂Cl₂, -70 deg C, 2) CH₂Cl₂, HOAc, -70 deg C to r.t.

3: 1) 2,4-lutidine, SOCl₂, 2) silica gel / 1) THF, -30 deg C to 0 deg C, 2) THF, 15 h

With thionyl chloride; 2,4-lutidine; silica gel; ozone; triethylamine; zinc; triethyl phosphite;

DOI:10.1039/c39820000933

upstream raw materials:

triphenylphosphine

methyl 6-phenoxyacetamidopenicillanate-1β-oxide

methyl α-(4R-acetylthio-3S-methoxy-3-phenoxyacetamido-2-azetidinon-1-yl)-β-methylcrotonate

methyl 6α-methoxy-6β-phenoxyacetamidopenicillanate-1β-oxide

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