97363-07-0

Upstream product

• 117901-06-1 (2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester 
• 117901-04-9 (2S,3S)-3-((S)-1,2-Dihydroxy-ethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester 
• 117901-05-0 (2S,3S)-1-(4-Methoxy-phenyl)-3-(S)-oxiranyl-4-oxo-azetidine-2-carboxylic acid tert-butyl ester 
• 117901-02-7 [[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranecarbonyl]-(4-methoxy-phenyl)-amino]-acetic acid tert-butyl ester 
• 117901-03-8 (2S,3S)-3-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-ethyl]-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 203790-60-7 (3S,4S)-3-{[(1'R)-1'-t-butyldimethylsilyloxy]ethyl}-4-ethoxycarbonyl-1-p-methoxyphenyl-2-azetidinone 
• 92685-90-0 (2S,3S)-3-((R)-1-Hydroxy-ethyl)-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carboxylic acid tert-butyl ester 
• 101905-26-4 (1'R,3S,4R)-3-<1'-((tert-butyldimethylsilyl)oxy)ethyl>-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 205525-21-9 (1'S,3S)-3-(1'-hydroxyethyl)-1-(4'-methoxyphenyl)-4-(2'-phenylethenyl)-2-azetidinone 
• 80542-40-1 N-cinnamylidene-p-anisidine 

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 academic research and scientific papers

Practical synthetic approach to 4-acetoxy-2-azetidinone for the preparation of carbapenem and penem antibiotics

A practical synthesis of 4-acetoxy-2-azetidinone useful for the preparation of carbapenem- and penem-type antibiotics is described. The synthesis has advantages such as avoiding the tedious and costly column chromatographic or recrystallized separation steps for diastereomers. The overall yield of the product is greatly improved and the process is also more economical for large-scale production. In addition, the mechanism for oxidative decarboxylation is also present. Springer Science+Business Media B.V. 2011.

PROCESSES FOR THE PREPARATION OF PENEMS AND ITS INTERMEDIATE

The present invention relates to a process for the preparation of 4-acetoxy azetidinone of Formula I, wherein R2 is hydrogen or a suitable amino protecting group and P is suitable hydroxy protecting group, and to the use of these compounds as intermediates for the preparation of ?-lactam antibiotics that possess the carbapenem and penem ring systems. 4-acetoxy azetidinone of Formula I is a key intermediate in the synthesis of ?-lactam antibiotics which are commonly prescribed antimicrobial agents having activity against a wide range of both Gram-positive and Gram-negative bacteria.

A NEW ENANTIO AND DIASTEREOSELECTIVE SYNTHESIS OF 2-AZETIDINONES AS USEFUL INTERMEDIATES OF β-LACTAM ANTIBIOTICS

An expeditious enantio and diastereoselective route to β-lactam synthons has been developed; two novel key radical reactions allowed us to obtain two useful intermediates in the synthesis of thienamycin and PS-5.

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.