Sd. Cao et al., STEREOSELECTIVE PHASE-TRANSFER-CATALYZED SYNTHESES OF GLYCOSYLOXYSUCCINIMIDES AND THEIR TRANSFORMATIONS INTO GLYCOPROBES, Tetrahedron, 51(24), 1995, pp. 6679-6686
Glycosyloxysuccinimides of D-galactose, D-glucose, N-acetyl-D-glucosam
ine, Lactose, maltose (7-11) and sialic acid (13) were prepared from t
heir glycosyl halides under PTC conditions. Ring opening of the succin
imide moieties occurred with sodium hydroxide or methoxide to provide
extended aglycons, while treatment of 8 with hydrazine afforded O-gala
ctopyranosylhydroxylamine 17. Treatment of 9 with tris(2-aminoethyl)am
ine gave divalent cluster 20 which upon further treatment with fluores
cein isothiocyanate provided divalent glycoprobe 21.