Structural Variations on N??acetylneuraminic acid, 20. Synthesis of some 2, 3??didehydro??2??deoxysialic Acids structurally varied at C??4 and their behavior towards …

E Schreiner, E Zbiral, RG Kleineidam…

Index: Schreiner, Erwin; Zbiral, Erich; Kleineidam, Reinhard G.; Schauer, Roland Liebigs Annalen der Chemie, 1991 ,  # 2  p. 129 - 134

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Abstract

Abstract The peracetylated methyl ester 1 of N-acetylneuraminic acid was transformed into the oxazoline derivative 2, which was hydrogenated with Pd/C/H 2 to give the 4-deoxy- Neu5Ac2en derivative 3. Acid cleavage of the oxazoline 2 by trifluoroacetic acid (THF) gave the 4-epi-Neu5Ac2en derivative 4a, which was saponified to the known 4-epi-Neu5Ac2en 4b. Treatment of 4a with triphenylphosphane/diethylazodicarboxylate (DEAD)/HN 3 in ...