Irvine‐Purdie Methylation

Abstract An exhaustive methylation of alkyl glycoside by repeated treatment of aforementioned glycoside with methyl iodide and silver oxide and the deprotection of anomeric alkyl group by hydrolysis of the resulting methyl saccharide ether with dilute acid is referred to as the Irvine–Purdie methylation. Additionally, this reaction also stands for the mere methylation of sugars from methyl iodide and silver oxide. It is often executed under mild conditions in a neutral solvent, in which the profound side reactions do not occur. This reaction has been modified to become the Haworth methylation, which has been further extended to treat sugars with sodium methylsulfinyl carbanion and methyl iodide for the purpose of per‐ O ‐methylation in one step. This reaction has been applied for the structural analysis of polysaccharide and the methylation of sugars.