(3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone

Base Information

• Chemical Name: (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone
• CAS No.: 100188-56-5
• Molecular Formula: C₁₂H₁₇NO₃SSi
• Molecular Weight: 283.423
• Mol file: 100188-56-5.mol

Synonyms:(3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone

Chemical Property of (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone

There total 4 articles about (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone 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: 85.0%

(3S,4R)-3-(trimethylsilyl)-4-(phenylthio)-2-azetidinone (100188-51-0) → (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone (100188-56-5)

Guidance literature:

(3S,4R)-3-(trimethylsilyl)-4-(phenylthio)-2-azetidinone; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 4.66667h; Inert atmosphere;

With sodium hydrogencarbonate; In dichloromethane; Inert atmosphere;

DOI:10.1021/ol902411r

Reference yield: 49.0%

sodium benzenesulfonate (873-55-2) + 3-(trimethylsilyl)-2-oxoazetidin-4-yl acetate (100188-48-5) → (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone (100188-56-5)

Guidance literature:

In water; acetone; at 25 ℃;

DOI:10.1021/jo00354a034

Reference yield:

(3S,4R)-3-(trimethylsilyl)-2-oxoazetidine-4-carboxylic acid (100188-47-4) → (3S,4R)-3-(trimethylsilyl)-4-(phenylsulfonyl)-2-azetidinone (100188-56-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 42 percent / diethyl ether

2: 1.38 g / acetic acid, lead tetracetate / dimethylformamide / 0.5 h / 54 °C

3: 49 percent / H₂O; acetone / 25 °C

With lead(IV) acetate; acetic acid; In diethyl ether; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00354a034

upstream raw materials:

sodium benzenesulfonate

3-(trimethylsilyl)-2-oxoazetidin-4-yl acetate

(3S,4R)-3-(trimethylsilyl)-2-oxoazetidine-4-carboxylic acid

(3S,4R)-3-(trimethylsilyl)-2-oxoazetidine-4-carboxylic acid methyl ester

Downstream raw materials:

(3S,4R)-3-(trimethylsilyl)-4-(phenylthio)-2-azetidinone