Design and Synthesis of Highly Bioactive Sugar-Related Substances

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The following research results have been obtained in this research project.1) Coyolosa which is a natural disaccharide having an unusual structure with a 6,6'-ether-linkage was successfully synthesized. In connection with its anti-diabetic activity, 10 kinds of analogs have been synthesized and it was concluded that the reported structure should be revised. A 6,6'-disaccharide formed from two molecules of mannose might be proposed.2) The conversion of sugar lactones to the hydroxamic acid derivatives by the ring opening operation and the recyclization under Mitsunobu conditions gives the corresponding L-sugar. By applying this conversion technique, L-ribose and L-iduronic acid were also synthesized efficiently3) Glycosylation using 1-methylenesugar afforded the corresponding α-D-glycoside stereo-selectively. This method could be applied to synthesize the various types of αglycosides such as α-oligosaccharides exhibiting a potent biological activity.