Studies on the Synthesis of C-Nucleosides--Synthesis of 3-β-D-XyIopyranosyl-1,2,4-Oxadiazoles

Abstract

Abstract: Fourteen new derivatives of 3-β-D-xylopyranosyl 1,2,4-oxadiazole were synthesized via condensating protected β-D-xylopyranosyl amidoxime with anhydrides or various substituted benzoyl chlorides in good yields.The 1,2,4-oxadiazole ring was formed directly by condensation of xylopyranosyl amidoxime and various anhydrides, but if the condensation occured by using substituted benzoyl chloride instead of anhydride, the cyclization was completed by two steps.The mechanism was discussed, 3-β-.D-xylopyranosyl-1,2,4-oxadiazole is stable under the condition of 1 mol/L HCl, 1 mol/L NaOH or at high temperature.

Key words: 1,2,4-Oxadiazole, Xylosyi C-nucleoside, Condensation reaction

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DONG Ling-jiao, LI Li, MA Ling-tai, ZHANG Li-he . Studies on the Synthesis of C-Nucleosides--Synthesis of 3-β-D-XyIopyranosyl-1,2,4-Oxadiazoles[J]. Chem. J. Chinese Universities, 1992, 13(5): 617.

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Studies on the Synthesis of C-Nucleosides--Synthesis of 3-β-D-XyIopyranosyl-1,2,4-Oxadiazoles

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