Facile synthesis of 2-deoxy-2-substituted D-arabinofuranose derivatives

TL Su, RS Klein, JJ Fox

Index: Su, Tsann-Long; Klein, Robert S.; Fox, Jack J. Journal of Organic Chemistry, 1981 , vol. 46, # 9 p. 1790 - 1792

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Citation Number: 30

Abstract

Several methyl 2-deoxy-2-substituted-~-arabinofuranosides (4a-e and 5b-e) to be used as intermediates in the synthesis of 2'-substituted arabinonucleosides of biomedical interest were prepared by treatment of methyl 3, 5-di-O-benzyl-2-O-(trifluoromethanesulfonyl)-a-and- 8-D-ribofuranosides 2 and 3 with the lithium, sodium, or tetrabutylammonium salts of various nucleophiles (I?-, C1-, Br-, I-, Ns-). While the a anomer 2 could be readily converted into ...