(+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone

Base Information

• Chemical Name: (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone
• CAS No.: 78902-62-2
• Molecular Formula: C₁₅H₂₃NOSSi
• Molecular Weight: 293.505
• Mol file: 78902-62-2.mol

Synonyms:(+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone

Chemical Property of (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone

There total 8 articles about (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-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: 98.0%

4-(phenylthio)azetidin-2-one (31898-69-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone (78902-62-2)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 1.5h;

DOI:10.1248/cpb.29.1854

Reference yield: 88.0%

3-(phenylsulfinyl)propionamide (49639-35-2,114462-98-5,114462-99-6) + ketene t-butyldimethylsilyl methyl acetal (77086-38-5) → (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone (78902-62-2)

Guidance literature:

zinc(II) iodide; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1248/cpb.39.2225

Reference yield:

methyl 3-phenylthiopropanoate (22198-59-0) → (+/-)-1-(tert-butyldimethylsilyl)-4-phenylthio-2-azetidinone (78902-62-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 67 percent / aq. KOH / ethanol / 1 h / Heating

2: DMF, SOCl₂ / 1 h / Heating

3: 28percent aq. NH₄OH / 1 h / 0 °C

4: 93 percent / NaIO₄ / methanol / Ambient temperature

5: 88 percent / ZnI₂ / acetonitrile / 1 h / Ambient temperature

With potassium hydroxide; ammonium hydroxide; sodium periodate; thionyl chloride; N,N-dimethyl-formamide; zinc(II) iodide; In methanol; ethanol; acetonitrile;

DOI:10.1248/cpb.39.2225

upstream raw materials:

3-(phenylsulfinyl)propionamide

ketene t-butyldimethylsilyl methyl acetal

4-(phenylthio)azetidin-2-one

tert-butyldimethylsilyl chloride

Downstream raw materials:

3-trimethylsilyl-4-thiophenyl-1-tert-butyldimethylsilylazetidin-2-one

2-[1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-yl]-2-phenylsulfanyl-malonic acid dimethyl ester

N-(tert-butyldimethylsilyl)-4-(phenylsulfinyl)azetidin-2-one

(3S*,4R*)-N-(tert-butyldimethylsilyl)-3-ethyl-4-(phenylthio)azetidin-2-one