Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Sialic Acids. XI. : Synthesis of 2-O-Clycosyl Derivatives of N-Acetylneuraminic Acid
SHINGO SATOKIMIO FURUHATAMASAYOSHI ITOHYOSHIYASU SHITORIHARUO OGURA
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Keywords: hydrolysis
JOURNAL FREE ACCESS

1988 Volume 36 Issue 3 Pages 914-919

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Abstract

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.

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© The Pharmaceutical Society of Japan
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