A Regio- and Stereo-selective Parallel Synthesis of Five Types of Trigalactoses on a Solid Support as a Model of a Combinatorial Oligosaccharide Library
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概要
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A regio- and stereo-selective parallel synthesis of oligosaccharides on a solid support was successfully achieved by a combination of a novel <I>α</I>-selective glycosidation procedure and a uni-chemo hydroxyl protection (UCHP) procedure. The <I>α</I>-selective glycosidation of dibutyl 3,4-di-<I>O</I>-benzoyl-2,6-di-<I>O</I>-benzyl-<I>α</I>/<I>β</I>-D-galactopyranosyl phosphate in cyclopentyl methyl ether (as an ethereal solvent for effective swelling of the polystyrene resin) proceeded smoothly and in relatively high yield. Five types of trigalactoses [Gal<I>α</I>1-3Gal<I>β</I>1-3Gal, Gal<I>β</I>1-3(Gal<I>α</I>1-4)Gal, Gal<I>α</I>1-4Gal<I>β</I>1-3Gal, Gal<I>α</I>1-3Gal<I>β</I>1-4Gal, and Gal<I>α</I>1-4Gal<I>β</I>1-4Gal] were successfully synthesized on a solid support as a model of a combinatorial oligosaccharide library.
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