Stereoselective synthesis of the alpha-glycoside of a KDO "C"-disaccharide.
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.
Koketsu
M
M
Departments of Chemistry, Medicinal and Natural Products Chemistry, Chemical and Biochemical Engineering, University of Iowa, Iowa City, Iowa 52242, USA.
Kuberan
B
B
Linhardt
R J
RJ
D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular
D004187:Disaccharides; D006027:Glycosides