Abstract
2-Hydroxyethyl 2,3,4-tri- O-acetyl-β- D-xylopyranoside was prepared from 2,3,4-tri- O-acetyl-α- D-xylopyranosyl chloride by the action of 1,2-ethanediol and mercuric acetate. Subsequent mesylation and azide displacement gave 2-azidoethyl 2,3,4-tri- O-acetyl-β- D-xylopyranoside, which was hydrogenated over palladiumon-charcoal and the amine acylated with various haloacetyl halides, to afford 2-(haloacetamido)ethyl 2,3,4-tri- O-acetyl-β- D-xylopyranosides. Deprotection to obtain the free sugars was carried out with 5m M ethanolic sodium ethoxide. 2-(Chloroacetamido)ethyl 2,3,4-tri- O-acetyl-β- D-xylopyranoside was further modified by sequential azide displacement, hydrogenation, and subsequent acylation with various haloacetyl halides to afford 2-[(haloacetamido)acetylamino]ethyl 2,3,4-tri- O-acetyl-β- D-xylopyranosides, which were also deprotected to give the corresponding free sugars. The effects of these haloacetamido analogs on the growth of the melanoma cells in tissue culture was evaluated.
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