Carbohydrate Research p. 209 - 218 (1984)
Update date:2022-08-05
Topics:
Ciucanu, Ionel
Kerek, Francisc
As a result of a study of the permethylation of sugars in such dipolar aprotic solvents as methyl sulphoxide, the hitherto accepted role of the CH3SOCH2- anion is questioned.The HO- and H+ ions appear to be the effective basic agents in these methylation reactions.This conclusion suggested a new method for the permethylation of sugars involving methyl iodide, a solid base (NaOH, KOH, or tert-BuOH/NaOH), and methyl sulphoxide.Excellent yields (98 +/- 2 percent) of permethylation products were obtained in a remarkably short (6-7 min) reaction time.The non-sugar peaks that appear in gas chromatograms of the products of Hakomori methylation were absent when the new reagent was used.
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