141805-92-7

Basic information

• Product Name: (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
• Synonyms: (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one
• CAS NO: 141805-92-7
• Molecular Weight: 335.519
• Mol File: 141805-92-7.mol

Chemical Properties

• CAS DataBase Reference: (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one(141805-92-7)
• EPA Substance Registry System: (3S)-1-(4-methoxyphenyl)-[(1R)-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one(141805-92-7)

Safety Data

• Hazardous Substances Data: 141805-92-7(Hazardous Substances Data)

Upstream product

• 105729-41-7 3-(R)-t-butyldimethylsilyloxybutanoic acid 
• 32752-37-7 1,3,5-tris(4-methoxyphenyl)-1,3,5-triazinane 
• 107265-57-6 (R)-3-(tert-butyldimethylsiloxy)butanoyl chloride 
• 141805-91-6 (2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(methanesulfonyl)methyl>-N-(4-methoxyphenyl)butylamide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 109323-90-2 (1'R,3S)-3-<1'-<(tert-butyldimethylsilyl)oxy>ethyl>azetidin-2-one 
• 141805-88-1 (4R)-3-<(2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(benzyloxy)methyl>butanoyl>-4-isopropyl-1,3-thiazolidine-2-thione 
• 141805-89-2 (2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-<(benzyloxy)methyl>-N-(4-methoxyphenyl)butylamide 
• 141805-87-0 (4R)-3-<(2S,3R)-3-Hydroxy-2-<(benzyloxy)methyl>butanoyl>-4-isopropyl-1,3-thiazolidine-2-thione 
• 141805-90-5 (2S,3R)-3-<(tert-Butyldimethylsilyl)oxy>-2-(hydroxymethyl)-N-(4-methoxyphenyl)butylamide 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 104524-19-8 methyl (R)-(-)-3-(tert-butyldimethylsilyloxy)butyrate 

Downstream Products

• 1335557-95-3 (3S)-1-(4-methoxyphenyl)-[(1R)-(4-phenylbutoxy)ethyl]azetidin-2-one 
• 1335557-94-2 (3S)-1-(4-methoxyphenyl)-[(1R)-hydroxyethyl]azetidin-2-one 

Relevant articles and documents

SAR and LC/MS studies of β-lactamic inhibitors of human fatty acid amide hydrolase (h FAAH): Evidence of a nonhydrolytic process

The endocannabinoid hydrolyzing enzyme FAAH uses a nonclassical catalytic triad (namely, Ser-Ser-Lys instead of Ser-Asp-His) to cleave its endogenous substrates. Because inhibiting FAAH has a clear therapeutic potential, we previously developed β-lactam-t

A practical synthesis of a key intermediate for the production of β- lactam antibiotics

N-(p-methoxyphenyl)-hexahydro-1,3,5-triazine in presence of a Lewis acid and (R)-3-(t-butyldimethylsilyloxy)butyric acid chloride with Et3N directly furnish (3S,1'R)-N-p-methoxyphenyl-3-(l-t- butyldimethylsilyloxy)ethylazetidin-2-one with good diastereoselectivity. This product is transformed into the 4-acetoxy-azetidinone 1, a key intermediate in the synthesis of β-lactam antibiotics.

β-Lactams. 3. Asymmetric Total Syntheis of New Non-Natural 1β-Methylcarbapenems Exhibiting Strong Antimicrobial Activities and Stability against Human Renal Dehydropeptidase-I

Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-ethyl>-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5.Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d).Compounds 17a,b were successfully converted to new, non-natural 1β-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.