Novel reversed cyclonucleoside analogues with a d-ribofuranose glycone

Two novel ribofuranose cyclonucleoside analogues have been synthesised by a route using 5-azido-5-deoxy-1,2- O-isopropylidene-α- d-ribofuranose as the starting material. This derivative was converted into two azole-reversed nucleosides, which were cyclised regiospecifically and stereospecifically by...

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Bibliographic Details
Published in:Carbohydrate research 1999-10, Vol.321 (3), p.190-196
Main Authors: Ewing, David F., Goethals, Gérard, Mackenzie, Grahame, Martin, Patrick, Ronco, Gino, Vanbaelinghem, Laurence, Villa, Pierre
Format: Article
Language:English
Subjects:
2,5-Epoxyimidazo[1,5- a][1,3]diazocine
5,8-Epoxy[1,2,3]triazolo-[1,5- a][1,3]diazocine
Reversed cyclonucleoside
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Summary:Two novel ribofuranose cyclonucleoside analogues have been synthesised by a route using 5-azido-5-deoxy-1,2- O-isopropylidene-α- d-ribofuranose as the starting material. This derivative was converted into two azole-reversed nucleosides, which were cyclised regiospecifically and stereospecifically by formation of a pentofuranosylamine. An alternative route, starting from a methyl β- d-ribofuranoside, was much less efficient, reflecting the need for the correct anomeric configuration in the cyclisation step.
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(99)00189-5