Synthesis of 1-(D-Apio-β-D-furanosyl)-1,2,3-triazoles

Friedrich Hammerschmidt; Johann-Peter Polsterer; Erich Zbiral

doi:10.1055/s-1995-3921

Synthesis 1995; 1995(4): 415-418
DOI: 10.1055/s-1995-3921

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Synthesis of 1-(D-Apio-β-D-furanosyl)-1,2,3-triazoles

Friedrich Hammerschmidt^* , Johann-Peter Polsterer, Erich Zbiral

^*Institut für Organische Chemie der Universität Wien, Währingerstraße 38, A-1090 Wien, Austria

Abstract

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1,2,3-Tri-O-acetyl-3’-O-benzoyl-D-apio-D-furanose (2) [β-2: α-2 =1.8:1], conveniently available in three steps from 2’,3’-O-isopropylidene-D-apio-β-D-furanose (1), is transformed to the glycosyl azides 3 upon reaction with trimethylsilyl azide. The anomer β-3, separated from the minor component α-3 by chromatography, is transformed to a series of protected 1,2,3-triazole nucleosides 5 of D-apio-β-D-furanose upon reaction with 2-oxoalkylidene triphenylphosphoranes 4. Compounds 5 are deprotected to the corresponding nucleoside analogues 6 by transesterification with sodium methoxide-methanol. The carboxamide derivative 6f, which is structurally related to the antibiotic virazol, is obtained by ammonolysis of the ester derivative 6e.

β-D-Apionucleosides with substituted 1,2,3-triazoles as nucleobases were prepared.

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