Beilstein J. Org. Chem.2017,13, 2078–2086, doi:10.3762/bjoc.13.205
: bicyclonucleosides; biocatalysis; lipase; Novozyme®-435; separation of epimers; Introduction
Sugar-modified bicyclic nucleosides have drawn the attention of synthetic chemists because of their effect on the conformational restriction of the furanose moiety of the nucleoside [1][2][3][4][5][6][7][8][9]. The
conformational restriction has led to the enhancement in target selectivity and in vivo stability of the nucleoside-based drug candidates. One of the important precursors for the synthesis of different types of bicyclonucleosides is 4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-ribofuranose. The synthesis of the
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Graphical Abstract
Scheme 1:
Formation of a 1:1 epimeric mixture of 3a and 3b.