3-(1-Hydroxyethyl)-4-[(triphenylmethyl)sulfanyl]azetidin-2-one

Base Information

• Chemical Name: 3-(1-Hydroxyethyl)-4-[(triphenylmethyl)sulfanyl]azetidin-2-one
• CAS No.: 75939-72-9
• Molecular Formula: C24H23NO2S
• Molecular Weight: 389.518
• DSSTox Substance ID: DTXSID30509672

Synonyms:75939-72-9;SCHEMBL9385185;DTXSID30509672;3-(1-Hydroxyethyl)-4-[(triphenylmethyl)sulfanyl]azetidin-2-one

Chemical Property of 3-(1-Hydroxyethyl)-4-[(triphenylmethyl)sulfanyl]azetidin-2-one

Chemical Property:

• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 389.14495015
• Heavy Atom Count: 28
• Complexity: 475

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1C(NC1=O)SC(C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4)O

Technology Process of 3-(1-Hydroxyethyl)-4-[(triphenylmethyl)sulfanyl]azetidin-2-one

There total 2 articles about 3-(1-Hydroxyethyl)-4-[(triphenylmethyl)sulfanyl]azetidin-2-one 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: 80.0%

1-(Trimethylsilyl)-4-tritylthio-2-azetidinone (75939-71-8) + acetaldehyde (75-07-0,9002-91-9) + diisopropylamine (108-18-9) + lithium diisopropyl amide (4111-54-0) → 3-(1'-hydroxy-1'-ethyl)-4-tritylthio-2-azetidinone (75939-72-9)

Guidance literature:

With n-butyllithium; ammonium chloride; In tetrahydrofuran; hexane;

Reference yield:

→ 3-(1'-hydroxy-1'-ethyl)-4-tritylthio-2-azetidinone (75939-72-9)

Guidance literature:

Reference yield: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + racemic (3S,4R)-3-((R)-1-hydroxyethyl)-4-triphenylmethylthio-2-azetidinone (75939-72-9,75992-00-6,75992-01-7,79645-54-8,79645-55-9,87037-99-8) → racemic (3S,4R)-3-((R)-1-(t-butyldimethylsilyloxy)ethyl)-4-triphenylmethylthio-2-azetidinone (87996-93-8,88035-31-8,93603-69-1)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)92144-1

upstream raw materials:

1-(Trimethylsilyl)-4-tritylthio-2-azetidinone

acetaldehyde

diisopropylamine

lithium diisopropyl amide

Downstream raw materials:

racemic (3S,4R)-3-((R)-1-(t-butyldimethylsilyloxy)ethyl)-4-triphenylmethylthio-2-azetidinone

racemic p-nitrobenzyl (5R,6S)-6-((R)-1-(t-butyl-dimethylsilyloxy)ethyl)-2-methylthiopenem-3-carboxylate

racemic p-nitrobenzyl (3S,5R,6S)-6-((R)-1-(t-butyl-dimethylsilyloxy)ethyl)-2-thioxopenam-3-carboxylate

racemic (3S,4R)-1-(p-nitrobenzyloxycarbonyl)methyl-3-<((R)-1-t-butyldimethylsilyloxy)-ethyl>-4-phenoxy(thiocarbonyl)thio-2-azetidinone

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