A novel approach to functionalization of allyl aglycon. Effective synthesis of selectively protected 2-aminoethyl lactoside, a common building block for the synthesis of carbohydrate chains of glycolipids

A novel approach to the functionalization of aglycon in allyl glycosides is described. The method comprises ozonolysis of the double bond in the allyl group, leading to the corresponding aldehyde, and subsequent transformatio n of the latter into the corresponding oxime, which is finally reduced to g ive the amine. The efficiency of this synthetic sequence (yield similar to 90%) is exemplified by the transformation of two allyl lactoside derivative s into selectively protected 2-aminoethyl lactosides. The latter are conven ient common building blocks for the synthesis of carbohydrate chains of gly colipids that have a lactose unit at the reducing end.