Abstract
Some N-acetyl-D-neuraminec acid nucleoside analogs were synthesized. Methyl penta-O-acetyl-N-acetyl-D-neuraminate (1) was treated with trimethylsilyl-pyrimidine or -5-fluoropyrimidine and tin(IV) chloride to give a mixture of α- and β-anomers of N-nucleoside analogs. On the other hand, methyl tetra-O-acetyl-N-acetyl-2-chloro-β-D-neuraminate was allowed to react with trimethylsilyl-pyrimidine or -5-fluoropyrimidine under the Koenigs-Knorr reaction conditions to provide the β-anomer in a fair yield. The stereochemistry of these compounds was confirmed by measurements of the rate of hydrolysis of the glycosidic bond with water.
