Irvine-Purdie methylation

What is Irvine-Purdie methylation?

The Irvine-Purdie methylation, also referred to as Purdie methylation, is a chemical reaction that involves the exhaustive methylation of a methyl glycoside.

Purdie methylation - general reaction scheme - Irvine-Purdie methylation
Irvine-Purdie methylation

This is achieved by subjecting the glycoside to repeated treatment with methyl iodide MeI and silver oxide, Ag2O, followed by hydrolysis of the resulting pentamethyl ether using dilute acid. The Irvine-Purdie methylation yields the anomeric hydroxyl group.

References

T. Purdie, J. C. Irvine, “C.—The alkylation of sugarsJ. Chem. Soc., Trans., 1903, 83, 1021-1037 DOI: 10.1039/CT9038301021

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