Abstract
Anomeric pairs of 3-(2-aminoethylthio)propyl d-galactopyranoside ( 4, 4a), d-glucopyranoside ( 5, 5a), and 2-acetamido-2-deoxy- d-glucopyranoside ( 6, 6a) were prepared by addition of 2-aminoethanethiol to the corresponding, anomeric, allyl glycosides. The allyl α-glycosides were prepared by refluxing the sugars with allyl alcohol in the presence of an acid catalyst; the allyl β-glycosides were prepared by the reaction of acetylated glycosyl bromides with allyl alcohol in the presence of mercuric cyanide, followed by O-deacetylation. The rate of thiol addition to the allylic group was found to be different for each glycoside.
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