18997-19-8
Chemical Structure
Pivaloyloxymethyl chloride
- CAS No.: 18997-19-8
- Formula:C6H11ClO2
- Molecular Weight:150.60
IUPAC Name: chloromethyl pivalate
InChIKey: GGRHYQCXXYLUTL-UHFFFAOYSA-N
SMILES: CC(C)(C)C(OCCl)=O
Biological Activity: Pivaloyloxymethyl chloride is an organic intermediate used to introduce the pivaloyloxymethyl (POM) protecting group, and it can be prepared from trimethylacetic acid and chloromethyl chlorosulfonate as raw materials. Pivaloyloxymethyl chloride is an alkylating reagent for the synthesis of phosphonic acid prodrugs; the introduction of the hydrophobic POM group enhances the lipid solubility and membrane permeability of molecules. Pivaloyloxymethyl chloride can be used in the synthesis of tetrakis (pivaloyloxymethyl) methylenebisphosphonate, which is a precursor of the pivaloyloxymethyl clodronate prodrug. Pivaloyloxymethyl chloridecan support the synthesis of aryl/pivaloyloxymethyl mixed phosphonate prodrugs of butyrophilin 3A1 ligands[1][2].
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Pivaloyloxymethyl chloride | 99.98% | Pivaloyloxymethyl chloride is an organic intermediate used to introduce the pivaloyloxymethyl (POM) protecting group, and it can be prepared from trimethylacetic acid and chloromethyl chlorosulfonate as raw materials. Pivaloyloxymethyl chloride is an alkylating reagent for the synthesis of phosphonic acid prodrugs; the introduction of the hydrophobic POM group enhances the lipid solubility and membrane permeability of molecules. Pivaloyloxymethyl chloride can be used in the synthesis of tetrakis (pivaloyloxymethyl) methylenebisphosphonate, which is a precursor of the pivaloyloxymethyl clodronate prodrug. Pivaloyloxymethyl chloridecan support the synthesis of aryl/pivaloyloxymethyl mixed phosphonate prodrugs of butyrophilin 3A1 ligands. | ||||||||||||||||||||
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- [1]. Foust BJ, Poe MM, Lentini NA, et al.. Mixed Aryl Phosphonate Prodrugs of a Butyrophilin Ligand. ACS medicinal chemistry letters. 2017 Sep 14;8(9):914-918. [Content Brief]
- [2]. Niemi R, Vepsäläinen J, Taipale H and, et al.. Bisphosphonate prodrugs: synthesis and in vitro evaluation of novel acyloxyalkyl esters of clodronic acid. Journal of medicinal chemistry. 1999 Dec 02;42(24):5053-8. [Content Brief]
Keywords
