Stereoselective Synthesis of the Hexasaccharide Repeating Unit of the Cell Wall Polysaccharide from Kineosporia aurantiaca VKM Ac-720T Employing the Direct Glycosylation with Anomeric Hydroxy Sugars Involving Glycosyl Phthalate Intermediates
2009
Synthesis of a suitably protected form of the hexasaccharide repeating unit of the cell wall polymer from Kineosporia aurantiaca VKM Ac-720 T has been achieved by the stereoselective direct glycosylation of a trisaccharide acceptor with a trisaccharide donor having an anomeric hydroxy group involving a glycosyl phthalate intermediate. Both the trisaccharide acceptor and the trisaccharide donor were obtained from a common trisaccharide, of which two β-mannopyranosyl linkages were constructed stereoselectively by employing the direct glycosylation method with the anomeric hydroxy sugar involving a glycosyl phthalate intermediate and the 2′-carboxybenzyl glycoside method, respectively.
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