85281-73-8

Basic information

• Product Name: (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone
• Synonyms: (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone
• CAS NO: 85281-73-8
• Molecular Weight: 337.558
• Mol File: 85281-73-8.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone(85281-73-8)
• EPA Substance Registry System: (3S,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)-ethyl]-4-phenylthio-2-azetidinone(85281-73-8)

Safety Data

• Hazardous Substances Data: 85281-73-8(Hazardous Substances Data)

Upstream product

• 120705-88-6 tert-Butyl-dimethyl-((R)-1-methyl-3-phenylsulfanyl-propoxy)-silane 
• 134641-08-0 (R)-4-(phenylthio)-2-butanol 
• 930-69-8 sodium thiophenolate 
• 83204-40-4 (2S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83204-40-4 (2S,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 83162-13-4 (2S,6S)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-6-phenylselanyl-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 123994-10-5 (2S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 123994-10-5 (2S,6R)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 76431-32-8 methyl 6α-bromo,6β-1'-(R)-hydroxyethyl penicillanate 
• 74189-21-2 (2S,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester 
• 62263-73-4 (2S,6R)-6-((R)-1-Hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 105397-25-9 (3S,4R)-4-(Methylsulfonyl)-3-<(R)-1-(tert-butyldimethylsiloxy)ethyl>-1-(1-(methoxycarbonyl)-2-methyl-1-propenyl)-2-azetidinone 
• 85281-79-4 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-phenylsulfanyl-azetidin-2-one 
• 85281-80-7 (3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((S)-1-hydroxy-ethyl)-4-phenylsulfanyl-azetidin-2-one 

Downstream Products

• 128624-91-9 2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-2-phenylsulfanyl-malonic acid dimethyl ester 
• 138332-40-8 (3S,4R)-4-benzoylthio-3-<(1R)-(1-tert-butyldimethylsiloxy)ethyl>-azetidin-2-one 
• 128624-94-2 (6S,7S)-7-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-chloromethyl-2,2-dimethyl-5-phenylsulfanyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one 
• 128624-92-0 (3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(2-hydroxy-1-hydroxymethyl-1-phenylsulfanyl-ethyl)-azetidin-2-one 
• 128624-93-1 (3S,4S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-(2-chloro-1-hydroxymethyl-1-phenylsulfanyl-ethyl)-azetidin-2-one 
• 142407-58-7 (3R,4R)-4-benzyloxy-3-<(1R)-1-tert-butyldimethylsilyloxyethyl>azetidin-2-one 
• 114156-44-4 (3S,4R)-1-<<(benzyloxy)carbonyl>methyl>-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-4-(phenylthio)-2-azetidinone 
• 114156-43-3 (3S,4R)-3-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-1-<(methoxycarbonyl)methyl>-4-(phenylthio)-2-azetidinone 
• 144069-72-7 (3S,4R)-3-<(1R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-phenylsulfinylazetidin-2-one 
• 383186-38-7 (3S,4R)-4-benzenesulfonyl-3-((1R)-1-(tert-butyldimethylsilanyloxy)-ethyl)-azetidin-2-one 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 90776-58-2 (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(RS)-1-(hydroxycarbonyl)ethyl]-2-azetidinone 
• 135297-16-4 (3S,4R)-3-<(1R)-1-tert-butyldimethylsiloxyethyl>-4-(2-oxocyclohexyl)azetidin-2-one 
• 114247-25-5 benzyl (2R,6R,7S)-7-<(R)-1'-<(tert-butyldimethylsilyl)oxy>ethyl>-8-oxo-1-azabicyclo<4.2.0>octane-2-carboxylate 

Relevant articles and documents

β-lactams derived from a carbapenem chiron are selective inhibitors of human fatty acid amide hydrolase versus human monoacylglycerol lipase

A library of 30 β-lactams has been prepared from (3R,4R)-3-[(R)- 1′-(tbutyldimethylsilyloxy)-ethyl]-4-acetoxy-2-azetidinone, and the corresponding deacetoxy derivative, by sequential N- and O-functionalizations with various ω-alkenoyl and ω-arylalkanoyl c

An efficient synthesis of 4-heterofunction-substituted 3-(1-hydroxy)ethylazetidin-2-ones from 3-(1-hydroxy)ethyl-4-phenylsulfinylazetidin-2-one by reaction with silylated heteronucleophiles

3-(1-tert-Butyldimethylsiloxy)ethyl-4-sulfinylazetidin-2-one was reacted with silylated N-, S-, O-, and P-nucleophiles in the presence of a catalytic amount of ZnI2 to give the corresponding trans-4-heterofunction-substituted azetidin-2-ones in high yields.

A NOVEL SUBSTITUTION REACTION OF 4-SULFINYLAZETIDIN-2-ONE WITH SILYLATED HETERONUCLEOPHILES: AN EFFICIENT SYNTHESIS OF 4-HETEROFUNCTION SUBSTITUTED 3-(1-HYDROXY)ETHYLAZETIDIN-2-ONES

4-Sulfinylazetidin-2-one was reacted with silylated heteronucleophiles in the presence of a catalytic amount of zinc iodide to give the corresponding trans-4-heterofunction substituted azetidin-2-ones in high yields.