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Updated: Aug 23, 2025

Hierarchical and Programmable One-Pot Oligosaccharide Synthesis
Published on: September 6, 2019
Iterative Synthesis of Inulin-Type Fructooligosaccharides Enabled by Stereoselective β-d-Fructofuranosylation
Liang-Jing Zou1, Xing Yang1, Xi-Rui Zhao1
1Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Sichuan Province, Sichuan Engineering Laboratory for Plant-Sourced Drug and Sichuan Research Center for Drug Precision Industrial Technology, West China School of Pharmacy, Sichuan University, Chengdu 610041, P. R. China.
Abstract:
Inulin-type fructooligosaccharides (FOSs) constitute an abundant subgroup of fructans with important biological activities. However, the availability of individual fructooligosaccharides with an accurate structure in high purity and quality remains challenging. We herein report the first iterative synthesis of five inulin-type FOSs with degrees of polymerization ranging from 3 to 7 via highly stereoselective β-(2 → 1)-d-fructofuranosylation on a gram scale. Central to the synthesis is the decisive use of the 1-O-TIPS-6-O-picoloyl-protected fructofuranosyl thioglycoside donor, which assured the excellent β-selective glycosylation by the hydrogen-bond-mediated aglycone delivery (HAD).
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