((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester

Base Information

• Chemical Name: ((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester
• CAS No.: 87043-33-2
• Molecular Formula: C₃₄H₃₁N₂O₅PS
• Molecular Weight: 610.67

Synonyms:((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-(triphenyl-λ⁵-phosphanylidene)-acetic acid methyl ester

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

Useful:

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

There total 2 articles about ((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-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:

2-((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester (87305-51-9) → ((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (87043-33-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, 2.) Me₂CO₂H-Zn / 1.) CH₂Cl₂, -78 deg C

2: 1.) 2,6-lutidine, thionyl chloride, 2.) silica gel / 1.) THF, -30 deg C, 0 deg C, 2.) THF, 15 h

With 2,6-dimethylpyridine; thionyl chloride; Me₂CO₂H-Zn; silica gel; ozone;

DOI:10.1016/S0040-4039(00)81966-8

Reference yield:

((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-hydroxy-acetic acid methyl ester (87027-75-6,87068-91-5) + triphenylphosphine (603-35-0) → ((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (87043-33-2)

Guidance literature:

With 2,6-dimethylpyridine; thionyl chloride; silica gel; Yield given. Multistep reaction; 1.) THF, -30 deg C, 0 deg C, 2.) THF, 15 h;

DOI:10.1016/S0040-4039(00)81966-8

Reference yield: 75.0%

((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-(triphenyl-λ5-phosphanylidene)-acetic acid methyl ester (87043-33-2) → 2-benzyl-5(4H)-oxazolone (1078-60-0) + methyl 5-methylthiazole-4-carboxylate (68751-05-3) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

In toluene; at 80 ℃; for 48h;

DOI:10.1016/S0040-4039(00)81966-8

upstream raw materials:

((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-hydroxy-acetic acid methyl ester

triphenylphosphine

2-((2R,3S)-2-Acetylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-3-methyl-but-2-enoic acid methyl ester

Downstream raw materials:

2-benzyl-5(4H)-oxazolone

methyl 5-methylthiazole-4-carboxylate

Triphenylphosphine oxide

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