Oxidation of the primary hydroxyl group of galactose of galactaosyl ceramide analogue by chemical method—precursors for the synthesis of labeled conjugates

摘要

Isotopic labeling of the C-6 of a model glycosphingolipid (2S, 3R, 4E)-2-(1-adamantanacetamido)-3- hydroxy-4-octadecenyl-β-n-galactopyranoside, GalCAda, is described. Oxidation of (2S, 3R, 4E)-2-(1- adamantanacetamido)-3-(benzoyloxy)-4-octadeceny1-2,3,4-tri-O-benzoyl-6-o-galactopyranoside with o-iodoxybenzoic acid gave the dialdoside derivative in good yield. Reduction of the dialdoside with sodium borodeuteride gave the deuterium labeled D-GalCAda, with a cumulative yield of 35%.