Description

(R)-1-(tert-Butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid (CAS No. 162856-35-1) is a high-purity, chiral azetidine derivative featuring a tert-butyldimethylsilyl (TBS) protecting group and a reactive 4-oxoazetidine-2-carboxylic acid moiety. This compound, with the molecular formula C₁₀H₁₉NO₃Si, is a valuable building block in organic synthesis and medicinal chemistry, particularly for the preparation of β-lactam antibiotics and other heterocyclic scaffolds. Its IUPAC name is (2R)-1-[tert-butyl(dimethyl)silyl]-4-oxoazetidine-2-carboxylic acid, and it exhibits excellent stability under inert conditions. Suitable for researchers and pharmaceutical developers, this product is rigorously tested for purity (typically ≥95% by HPLC or NMR) and is available in various quantities to meet laboratory-scale or process-scale needs. Store in a cool, dry place under an inert atmosphere to maintain optimal stability.

Properties

• CAS Number: 162856-35-1
• Complexity: 306
• IUPAC Name: (2R)-1-[tert-butyl(dimethyl)silyl]-4-oxo-azetidine-2-carboxylic acid
• InChI: InChI=1S/C10H19NO3Si/c1-10(2,3)15(4,5)11-7(9(13)14)6-8(11)12/h7H,6H2,1-5H3,(H,13,14)/t7-/m1/s1
• InChI Key: LIEWITJXZYCDLE-SSDOTTSWSA-N
• Exact Mass: 229.11342000
• Molecular Formula: C10H19NO3Si
• Molecular Weight: 229.35
• SMILES: CC(C)(C)[Si](C)(C)N1[C@H](CC1=O)C(=O)O
• Topological: 57.6
• Monoisotopic Mass: 229.11342000
• Synonyms: 162856-35-1, (R)-1-(tert-Butyldimethylsilyl)-4-oxoazetidine-2-carboxylic acid, (2R)-1-(TERT-BUTYLDIMETHYLSILYL)-4-OXOAZETIDINE-2-CARBOXYLIC ACID, (4r)-n-(tert-butyldimethylsilyl)azetidin-2-one-4-carboxylic acid, (2R)-1-[tert-butyl(dimethyl)silyl]-4-oxoazetidine-2-carboxylic acid, 2-Azetidinecarboxylic acid, 1-[(1,1-dimethylethyl)dimethylsilyl]-4-oxo-, (2R)-, MFCD01862125, LIEWITJXZYCDLE-SSDOTTSWSA-N, SCHEMBL760161, DTXSID20370010, AKOS017343014, PS-20354, CS-0184544, P20973, (2R)-1-(tbdms)-4-oxoazetidine-2-carboxylic acid, (4R)-N-(tert-Butyldimethylsilyl)azetidin-2-one-carboxylic acid, (R)-1-(tert-Butyldimethylsilyl)-4-oxoazetidine-2-carboxylicacid, 1-(tert-butyldimethylsilyl)-4-oxoazetidine-2(R)-carboxylic acid, (r)-1-(tert-butyl-dimethyl-silanyl)-4-oxo-azetidine-2-carboxylic acid, 2-Azetidinecarboxylicacid,1-[(1,1-dimethylethyl)dimethylsilyl]-4-oxo-,(2R)-

Application

This compound serves as a key intermediate in the synthesis of chiral β-lactam antibiotics and other bioactive molecules. It is widely used in asymmetric synthesis and peptidomimetic research due to its rigid azetidine ring and carboxyl functionality. The TBS group enhances solubility and stability, making it ideal for multi-step synthetic routes in drug discovery.

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