{(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-oxo-propyl ester

Base Information

• Chemical Name: {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-oxo-propyl ester
• CAS No.: 81976-48-9
• Molecular Formula: C₄₀H₃₇N₂O₁₂PS
• Molecular Weight: 800.78

Synonyms:{(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-oxo-propyl ester

Chemical Property of {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-oxo-propyl ester

Chemical Property:

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Technology Process of {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-oxo-propyl ester

There total 6 articles about {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 2-oxo-propyl 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:

(R)-2-{(2R,3S)-2-((E)-1,4-Diacetoxy-but-2-ene-2-sulfinyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-3-methyl-but-3-enoic acid methyl ester → {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-oxo-propyl ester (81976-48-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N

2: PBr₃ / dimethylformamide / -20 °C

3: 1.) O₃, 2.) MeOH, silica gel

4: 2.) SOCl₂ / 2.) pyridine, 3.) THF, pyridine, 40 deg C

With methanol; thionyl chloride; silica gel; phosphorus tribromide; ozone; triethylamine; In N,N-dimethyl-formamide;

Reference yield:

2-{(2R,3S)-2-((E)-1,4-Diacetoxy-but-2-ene-2-sulfinyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester → {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-oxo-propyl ester (81976-48-9)

Guidance literature:

Multi-step reaction with 3 steps

1: PBr₃ / dimethylformamide / -20 °C

2: 1.) O₃, 2.) MeOH, silica gel

3: 2.) SOCl₂ / 2.) pyridine, 3.) THF, pyridine, 40 deg C

With methanol; thionyl chloride; silica gel; phosphorus tribromide; ozone; In N,N-dimethyl-formamide;

Reference yield:

(2S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (76602-58-9) → {(2R,3S)-2-(2-Acetoxy-acetylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-oxo-propyl ester (81976-48-9)

Guidance literature:

Multi-step reaction with 6 steps

2: 70 percent / toluene / Heating

3: Et₃N

4: PBr₃ / dimethylformamide / -20 °C

5: 1.) O₃, 2.) MeOH, silica gel

6: 2.) SOCl₂ / 2.) pyridine, 3.) THF, pyridine, 40 deg C

With methanol; thionyl chloride; silica gel; phosphorus tribromide; ozone; triethylamine; In N,N-dimethyl-formamide; toluene;

upstream raw materials:

acetonyl glyoxylate hydrate

triphenylphosphine

Acetic acid (2R,3S)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-2-ylsulfanylcarbonylmethyl ester

2-{(2R,3S)-2-((E)-3-Acetoxy-1-acetoxymethyl-propenylsulfanyl)-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester

Downstream raw materials:

(5R,6S)-3-Acetoxymethyl-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 2-oxo-propyl ester

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