Synthesis of inositol glycan cyclic phosphates.
An efficient synthesis of tri-, tetra-, and pentasaccharide cyclic phosphates 1-5, structurally related to natural inositol phosphate glycans, is reported. The title compounds were assembled by PhSeOTf-promoted glycosylation of the known glucosamine precursor, t-butyldimethylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-beta-D-glucopyranoside (8) with protected 1-methylthio mono-, di-, and trimannosides 7a-c, and, after conversion into glycosyl fluorides, Cp2ZrCl2- AgOTf-promoted glycosylation of differentially protected optically pure 1D-myo-inositol 11. The syntheses were completed by installing the cyclic phosphate moieties with methylpyridinium dichlorophosphate and finally, removal of all protecting groups by dissolving-metal reduction.
Jaworek
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Department of Chemistry, Tufts University, Medford, MA 02155, USA.
Iacobucci
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Calias
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d'Alarcao
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D005944:Glucosamine / Q000031:analogs & derivatives*; D007295:Inositol Phosphates / Q000138:chemical synthesis*; D007329:Insulin Antagonists / Q000138:chemical synthesis*; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000138:chemical synthesis*
D007295:Inositol Phosphates; D007329:Insulin Antagonists; D009844:Oligosaccharides; D011134:Polysaccharides; C028039:inositol phosphate glycan; D005944:Glucosamine