106399-62-6

Basic information

• Product Name: (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone
• Synonyms: (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone
• CAS NO: 106399-62-6
• Molecular Weight: 363.529
• Mol File: 106399-62-6.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone(106399-62-6)
• EPA Substance Registry System: (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone(106399-62-6)

Safety Data

• Hazardous Substances Data: 106399-62-6(Hazardous Substances Data)

Upstream product

• 205525-21-9 (1'S,3S)-3-(1'-hydroxyethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 80542-40-1 N-cinnamylidene-p-anisidine 
• 101905-26-4 (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 113396-67-1 (2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid methoxy-methyl-amide 

Downstream Products

• 203252-14-6 (2R,3R)-3-((R)-1-(tert-butyldimethylsilyloxy)ethyl)-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl acetate 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 

Relevant articles and documents

Asymmetric Synthesis of (1'R,3R,4R)-4-Acetoxy-3(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone and Other 3-(1'-Hydroxyethyl)-2-azetidinones from (S)-(+)-Ethyl 3-Hydroxybutanoate: Formal Total Synthesis of (+)-Thienamycin

The synthesis of (1'R,3R,4R)-4-acetoxy-3-(1'-((tert-butyldimethylsilyl)oxy)ethyl)-2-azetidinone, an important precursor for synthesis of carbapenems and penems, is detailed.The methodology utilized relies on the addition, cyclization reaction between the dianion of (S)-(+)-ethyl 3-hydroxybutanoate and N-arylaldimines.The syntheses of other useful optically active 3-(hydroxyethyl)-2-azetidinones are presented.A study of factors influencing the stereochemistry in the addition, cyclization reaction for the formation of 3-(1'-hydroxyethyl)-2-azetidinones is detailed.