Abstract
Various di- and trisaccharide precursors of the kijanimicin tetrasaccharide were prepared by the N-iodosuccinimide glycosylation procedure employing regioselectively blocked L-digitoxosides and L-digitoxals. Assumed 13-neighboring group participations were studied in acid- and silver or mercury salt-promoted glycosylations with selectively functionalized digitoxoses or their glycosyl chlorides. No evidence for enhanced β:α-ratios exceeding that of previous glycosylations in 2-deoxy-ribo components could be observed. A straightforward sequential synthetic approach applied both the studied glycosylation methods and thus a synthesis of the blocked D C B-A tetrasaccharide of kijanimicin was achieved. Throughout structures and conformations of the oligosaccharides were assigned by extensive 1H NMR spectroscopy.
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