Abstract
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 transformation of the latter into the corresponding oxime, which is finally reduced to give the amine. The efficiency of this synthetic sequence (yield ∼90%) is exemplified by the transformation of two allyl lactoside derivatives into selectively protected 2-aminoethyl lactosides. The latter are convenient common building blocks for the synthesis of carbohydrate chains of glycolipids that have a lactose unit at the reducing end.
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Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1308–1313, July, 2000.
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Kononov, L.O., Cheshev, P.E. & Nifant'ev, N.E. 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. Russ Chem Bull 49, 1305–1309 (2000). https://doi.org/10.1007/BF02495780
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DOI: https://doi.org/10.1007/BF02495780