N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

Base Information

• Chemical Name: N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide
• CAS No.: 133789-00-1
• Molecular Formula: C₂₃H₃₀N₂O₅SSi
• Molecular Weight: 474.653
• Mol file: 133789-00-1.mol

Synonyms:N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

Chemical Property of N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

There total 5 articles about N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide 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: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone (88002-47-5) → N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide (133789-00-1)

Guidance literature:

DOI:10.1021/jo971433w

Reference yield:

sodium benzenesulfonate (873-55-2) → N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide (133789-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / dimethylformamide / Ambient temperature

2: 77 percent / DIPEA / tetrahydrofuran

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)93376-8

Reference yield:

(3S,4S)-4-acetoxy-3-phenoxyacetamido-azetidin-2-one (35592-67-7) → N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide (133789-00-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / dimethylformamide / Ambient temperature

2: 77 percent / DIPEA / tetrahydrofuran

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)93376-8

upstream raw materials:

tert-butyldimethylsilyl chloride

(3R-trans)-3-phenoxyacetylamino-4-phenylsulfonyl-2-azetidinone

sodium benzenesulfonate

(3S,4S)-4-acetoxy-3-phenoxyacetamido-azetidin-2-one

Downstream raw materials:

N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-2-(2-fluoro-ethyl)-4-oxo-azetidin-3-yl]-2-phenoxy-acetamide

N-[(2S,3R)-2-Benzenesulfonyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-2-pent-4-enyl-azetidin-3-yl]-2-phenoxy-acetamide

N-((2S,3R)-2-Allyl-2-benzenesulfonyl-4-oxo-azetidin-3-yl)-2-phenoxy-acetamide