Stereoselective synthesis of the alpha-glycoside of a KDO "C"-disaccharide |
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| Authors: | Koketsu M Kuberan B Linhardt R J |
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| Institution: | Departments of Chemistry, Medicinal and Natural Products Chemistry, Chemical and Biochemical Engineering, University of Iowa, Iowa City, Iowa 52242, USA. |
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| Abstract: | The reaction of tert-butyl (4,5,7, 8-tetra-O-acetyl-3-deoxy-alpha-D-manno-2-octulopyranosyl chloride)onate donor 7 with the 6-formylgalactopyranoside acceptor 4 in the presence of SmI(2) provided only the KDO alpha-C-disaccharide 8. The bulky tert-butyl ester in the donor was used to reverse the stereochemical outcome of C-glycosylation, stereoselectively forming the alpha-"C"-disaccharide of KDO. |
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