Glycosyl hydroperoxides derived from 2-deoxysugars

Oxidation of 3,4,6-tri-O-benzyl-2-deoxy-d-glucose and d-galactose or their t-butyl glycosides to the corresponding glycosyl hydroperoxides can be performed with hydrogen peroxide in the presence of an acid catalyst. Several reaction conditions and their influence on the effectiveness of the oxidation are discussed. Separation of the α - and β-anomers of the glycosyl hydroperoxides was achieved through mixed peroxide formation by reaction of the hydroperoxide group with 2-methoxypropene and subsequent deprotection.

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