It serves as a key building block, often referred to as MAP (Meropenem Azetidinone Propionic acid) intermediate, in creating carbapenem antibiotics like meropenem. (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid (or related stereoisomers) is a crucial protected intermediate in the synthesis of meropenem, specifically forming the azetidinone core and side chain, with the TBS (tert-butyldimethylsilyl) group acting as a protecting group for the hydroxyethyl side chain, which is later deprotected to reveal the final antibiotic structure.
(R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid
| API Name | Meropenem |
|---|---|
| CAS No | 90776-58-2 |
| Molecular Formula | C14H27NO4Si |
| Molecular Weight | 301.45 g/mol |
| Synonyms | (2R)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanoic acid |
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Frequently Asked Questions
It serves as a key building block, often referred to as MAP (Meropenem Azetidinone Propionic acid) intermediate, in creating carbapenem antibiotics like meropenem. (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid (or related stereoisomers) is a crucial protected intermediate in the synthesis of meropenem, specifically forming the azetidinone core and side chain, with the TBS (tert-butyldimethylsilyl) group acting as a protecting group for the hydroxyethyl side chain, which is later deprotected to reveal the final antibiotic structure.
The CAS number of (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid is 90776-58-2.
The molecular formula of (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid is C14H27NO4Si.
The listed molecular weight of (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid is 301.45 g/mol.
(R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid is listed as being used in connection with the following API: Meropenem.
The listed synonym or IUPAC name for (R)-2-[(3S,4S)-3-[(R)-1-(tert-Butyldimethylsilyloxy)ethyl]-2-oxoazetidin-4-yl]propionic acid is (2R)-2-[(2S,3S)-3-[(1R)-1-[tert-butyl(dimethyl)silyl]oxyethyl]-4-oxoazetidin-2-yl]propanoic acid.