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Updated: Jul 16, 2026

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Stereocontrolled One-Carbon Homologation of d-Glucose and d-Galactose Skeletons
Andrey Yu Plodukhin1, Mark W Peczuh1
1Department of Chemistry, University of Connecticut, 55 N. Eagleville Rd. U3060, Storrs, Connecticut 06269 United States.
Abstract:
A synthetic strategy to convert protected six-membered ring pyranose sugars to seven-membered ring septanose sugars by a one-carbon homologation is reported. The key reaction in the sequence is a diastereoselective hydroboration-oxidation that sets the C5 stereogenic center of the septanose; stereocontrol is driven by reagent-substrate interactions and A1,2-strain. Glycosidation of the protected septanoses exclusively delivered methyl β-septanosides. The design of the new ring-expanded sugars reproduces the array of stereocenters of natural pyranoses from C1-C5 and will facilitate their application as glycomimetics.
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