Organic letters

Stereoselective Synthesis of the α-Glycoside of a KDO “C”-Disaccharide

M Koketsu, B Kuberan, RJ Linhardt

文献索引：Koketsu, Mamoru; Kuberan, Balagurunathan; Linhardt, Robert J. Organic Letters, 2000 , vol. 2, # 21 p. 3361 - 3363

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被引用次数: 21

摘要

The reaction of tert-butyl (4, 5, 7, 8-tetra-O-acetyl-3-deoxy-α-d-manno-2-octulopyranosyl chloride) onate donor 7 with the 6-formylgalactopyranoside acceptor 4 in the presence of SmI2 provided only the KDO α-C-disaccharide 8. The bulky tert-butyl ester in the donor was used to reverse the stereochemical outcome of C-glycosylation, stereoselectively forming the α-" C"-disaccharide of KDO.