Studies on Sialic Acids. XI. : Synthesis of 2-O-Clycosyl Derivatives of N-Acetylneuraminic Acid

抄録

The reactions of methyl N-acetyl-4, 7, 8, 9-tetra-O-acetyl-2-chloro-2-deoxy-β-D-neuraminate (2) with 2', 3'-di-O-acetylinosine (1) and with 2', 3'-di-O-acetyl-N-benzoylcytidine (8) under Koenigs-KOnorr-like reaction conditions geve the corresponding (2→5) linked disaccharide uncleoside analogues, in yields of 31% and 23% respectively. These nucleoside 5'-N-acetylneuraminic acid analogues were converted via saponification or ammonolysis into the final target compounds. The stereochemistry of these. compounds was confirmed by analysis. of the proton nuclear magnetic resonance (¹H-NMR) spectra and measurement of the rate of hydrolysis of the (2→5) glycosidic linkage.