203252-14-6

Basic information

• Product Name: 2-Azetidinone, 4-(acetyloxy)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-(4- methoxyphenyl)-, (3R,4R)-
• CAS NO: 203252-14-6
• Molecular Formula: C20H31NO5Si
• Molecular Weight: 393.555
• Mol File: 203252-14-6.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Azetidinone, 4-(acetyloxy)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-(4- methoxyphenyl)-, (3R,4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Azetidinone, 4-(acetyloxy)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-(4- methoxyphenyl)-, (3R,4R)-(203252-14-6)
• EPA Substance Registry System: 2-Azetidinone, 4-(acetyloxy)-3-[(1R)-1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-(4- methoxyphenyl)-, (3R,4R)-(203252-14-6)

Safety Data

• Hazardous Substances Data: 203252-14-6(Hazardous Substances Data)

Upstream product

• 64-19-7 acetic acid 
• 127-09-3 sodium acetate 
• 97363-07-0 (2S,3S)-3-((R)-1-((tert-butyldimethylsilyl)oxy)ethyl)-1-(4-methoxyphenyl)-4-oxoazetidine-2-carboxylic acid 
• 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 
• 117901-02-7 [[(2R,3R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-oxiranecarbonyl]-(4-methoxy-phenyl)-amino]-acetic acid tert-butyl ester 
• 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 
• 117901-05-0 (2S,3S)-1-(4-Methoxy-phenyl)-3-(S)-oxiranyl-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 
• 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 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 106399-62-6 (1'R,3S,4S)-3-(1'-(tert-butyldimethylsilyloxy)ethyl)-4-formyl-1-(4'-methoxyphenyl)-2-azetidinone 
• 80542-40-1 N-cinnamylidene-p-anisidine 

Downstream Products

• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 

Relevant articles and documents

Cu-OMS-2-catalyzed decarboxylation-acetoxylation of (3R,4R)-4-acid-3-[(R)- 1-((t-butyl-dimethylsilyl)oxy)-ethyl]-1-methoxyphenyl-2-azetidinone with NaBrO3/NaOAc

(3R,4R)-4-Acetoxy-3-[(R)-1((t-butyldimethylsilyl)oxy)-ethyl] -1-methoxyphenyl-2-azetidinone (an important precursor for the synthesis of carbapenem antibiotics) was synthesized under mild and green conditions catalyzed by Cu-OMS-2. Normal to excellent iso

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.