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Irvine-Purdie Methylation

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr341

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Irvine-Purdie Methylation. Comprehensive Organic Name Reactions and Reagents. 341:1526–1529.

Publication History

  1. Published Online: 15 SEP 2010

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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.

Keywords:

  • glycosides;
  • Haworth methylation;
  • Walden inversion;
  • polysaccharide