87037-95-4

Basic information

• Product Name: (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one
• CAS NO: 87037-95-4
• Molecular Weight: 173.169
• Mol File: 87037-95-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one(87037-95-4)
• EPA Substance Registry System: (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one(87037-95-4)

Safety Data

• Hazardous Substances Data: 87037-95-4(Hazardous Substances Data)

Upstream product

• 5883-82-9 2-((4-methoxyphenyl)amino)-1-phenylethanone 
• 86561-72-0 (2R,3R)-2,3-epoxybutanoic acid 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 82938-51-0 (2S,3S)-1-(tert-Butyl-dimethyl-silanyl)-3-(1-hydroxy-ethyl)-4-oxo-azetidine-2-carboxylic acid 
• 82938-52-1 (2S,3S)-3-Acetyl-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid 
• 131991-73-6 (2R,6R)-2--6-methyl-1,3-dioxan-4-one 
• 127680-55-1 (1S,3R,5R,6R)-8-aza-3-acetyl-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 131991-74-7 (2R,6R)-2-(benzyloxymethyl)-6-methyl-1,3-dioxan-4-ol 
• 130919-59-4 (1S,3R,5R,6R)-8-aza-3-<1-(S)-hydroxyethyl>-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 131991-75-8 (2R,4R)-2-(benzyloxymethyl)-4-methyl-2H,4H-1,3-dioxin 
• 131991-77-0 (1S,3R,5R,6R)-8-aza-3-(hydroxymethyl)-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 127680-54-0 (1S,3R,5R,6R)-8-aza-3-<1-(S)-benzyloxyethyl>-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-7-one 
• 115869-78-8 (S)-1-(4-Methoxy-phenyl)-3-((R)-1-nitrooxy-ethyl)-4-oxo-azetidine-2-carboxylic acid 
• 115869-79-9 (3S,4R)-4-acetoxy-1-p-methoxyphenyl-3-<(R)-1-nitroxyethyl>azetidin-2-one 

Downstream Products

• 59995-64-1 thienamycin 
• 1308777-60-7 C₁₅H₁₈N₄O₂ 
• 135297-22-2 (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 

Relevant articles and documents

Antibacterial Agents and Cystic Fibrosis: Synthesis and Antimicrobial Evaluation of a Series of N-Thiomethylazetidinones

The increasing emergence of multidrug-resistant microorganisms is one of the greatest challenges in the clinical management of infectious disease. New antimicrobial agents are therefore urgently required, particularly in the treatment of chronic and recurrent infections often associated with antibiotic-resistant pathogens, as in the case of cystic fibrosis (CF) patients. This study reports the antibacterial activity of a series of monocyclic β-lactams with an alkylidenecarboxyl chain or electron-withdrawing groups such as 4-OAc, 4-SAc, and 4-SO2Ph at the C4 position of the ring. N-Unsubstituted and N-thiomethyl derivatives were compared. A total of 33 azetidinones were tested for their activity against Gram-positive and Gram-negative bacterial clinical isolates. The combination of an N-thiomethyl group and a benzyl ester on the 4-alkylidene side chain were found to increase the potency against Gram-positive bacteria. The N-thiomethyl group clearly elevated the activity of 4-acetoxyazetidinones relative to the corresponding NH derivatives. The most active compounds showed minimum inhibitory concentration (MIC) values of 4 and 8mgL-1 against methicillin-resistant Staphylococcus aureus isolated from pediatric patients with CF.

π-Allyl palladium ring closure strategy for the synthesis of a 1β-methylcarbapenem intermediate

A new ring closure by π-allyl palladium methodology is utilized in the synthesis of a 1-β-methyl carbapenem intermediate from 2-acetoxy azetidinone in six steps (40% yield).

Ruthenium catalyzed process for preparing 4-acetoxyazetidinones

A simplified process for preparing 4-acetoxyazetidinones of formula (I): STR1 wherein Z is a hydrogen atom, a lower alkyl group or a hydroxyethyl group which may or may not be protected is disclosed. According to the invention, azetidinones of formula (II): STR2 wherein Z has the same meaning as defined above and Y is a hydrogen atom or a carboxyl group is reacted with acetic acid and an oxidizing agent in the presence of a ruthenium compound as a catalyst.