82938-53-2

Basic information

• Product Name: (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one
• CAS NO: 82938-53-2
• Molecular Weight: 173.169
• Mol File: 82938-53-2.mol

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(82938-53-2)
• EPA Substance Registry System: (3R,4R)-4-acetoxy-3-[(1R)-1-hydroxyethyl]azetidin-2-one(82938-53-2)

Safety Data

• Hazardous Substances Data: 82938-53-2(Hazardous Substances Data)

Upstream product

• 546-67-8 lead(IV) tetraacetate 
• 82938-51-0 C₁₂H₂₃NO₄Si 
• 127680-56-2 (3R,4R)-4-acetoxy-3-<(R)-1-formyloxyethyl>-2-azetidinone 
• 115869-80-2 (3S,4R)-4-acetoxy-3-<(R)-1-nitroxyethyl>azetidin-2-one 
• 120236-28-4 (1'R,3S)-3-<1'-(hydroxy)ethyl>-2-azetidinone 
• 64-19-7 acetic acid 
• 130919-57-2 (1S,5R,6R)-8-aza-5-methyl-2,4-dioxa-bicyclo<4.2.0>octan-3,7-dione 
• 5883-82-9 2-((4-methoxyphenyl)amino)-1-phenylethanone 
• 86561-72-0 (2R,3R)-2,3-epoxybutanoic acid 
• 92685-83-1 N-<(tert-butoxycarbonyl)methyl>-p-anisidine 
• 313986-32-2 (2S,3S)-4-Oxo-1-trimethylsilanyl-3-((R)-1-trimethylsilanyloxy-ethyl)-azetidine-2-carboxylic acid 
• 119687-63-7 (2R,3S,4S)-4-Amino-2-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 
• 788146-73-6 (2R,3S,4R)-4-Amino-2-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 
• 721881-77-2 (2R,3R,4R)-4-Amino-2-methyl-5-oxo-tetrahydro-furan-3-carboxylic acid methyl ester 

Downstream Products

• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 59995-64-1 thienamycin 
• 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 
• 1308777-60-7 C₁₅H₁₈N₄O₂ 

Relevant articles and documents

OSMIUM-CATALYZED OXIDATION OF β-LACTAMS WITH PEROXIDES

Osmium-catalyzed oxidation of β-lactams with peroxides in acetic acid gives the corresponding 4-acetoxy β-lactams, which are versatile synthetic intermediate of carbapenem antibiotics, in good to excellent yields.

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 represented by the formula [Ru(B)2 (L)]m wherein B is Cl, Br or l, m is a positive integer, and L is 1,5-cyclooctadiene, norbornadiene, cycloheptatriene, cyclooctatetraene or benzene which may or may not have a lower alkyl group as a substituent, as a catalyst.

A highly stereoselective synthesis of the 1β-methylcarbapenem key intermediate from (R)-3-hydroxybutyric acid

(3R,4R)-4-Acetoxy-3-[(R)-1-(formyloxy)ethyl]-2-azetidinone 6 could be prepared highly stereoselectivity from (R)-3-hydroxybutyric acid by employing the [2+2]-cycloaddition reaction of chlorosulfonyl isocyanate with the 2H,4H-1,3-dioxin derivative and the Baeyer-Villiger reaction accompanying novel cleavage of the acetal moiety. The Reformatsky reaction of 6 with sterically crowded 3-(2-bromopropionyl)-2-oxazolidone derivatives readily afforded the title key intermediate after sequential chemical manipulations.

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.

Stereospecific Synthesis of a Chiral Intermediate for the Preparation of Thienamycin, Penems, and Carbapenems: Use of the Nitro Group as a Hydroxy Protecting Group

A total stereo- and enantio-controlled synthesis of (3S,4R)-4-acetoxy-3-azetidin-2-one (1) from ethyl (S)-3-hydroxybutyrate is reported.A simple method of inversion and concomitant protection of the hydroxy function in the side chain i