New Synthesis ofl-Ribofuranose Derivatives froml-Arabinose

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Abstract
There is a need for l-ribofuranose derivatives suitable for the preparation of l-nucleosides which could be employed to build nucleases resistant ‘antisense’ oligonucleotides1 and to prepare analogues as potential inhibitors of HIV.2 Such l-ribofuranoside derivatives were previously obtained by epimerisation at C-2 of l-arabinose in the presence of molybdenic acid3 and by inversion of configuration at C-2 of l-arabinose and C-3 of l-xylose by nucleophilic displacement of a sulfonate group.4 In both cases, the desired l-ribofuranoside derivative has to be separated from some remaining starting material. Another method to obtain l-ribose involved the complete inversion of d-ribono-1,4-lactone followed by reduction.5 We report herein a new transformation of l-arabinose into l-ribofuranose derivatives.