What question did this study set out to answer?

The aim is to achieve a stereoselective synthesis of glucosides from glycosyl hemiacetals using lithium iodide.

February 8, 2026The Journal of Organic Chemistry0 citations

Stereoselective α-Glucosylations from Glycosyl Hemiacetals Mediated by Lithium Iodide and Synthesis of the Pentasaccharide Repeating Unit of FPS-1

OPOana G. PopaUniversity College Dublin IPImlirenla PongenerUniversity College Dublin DPDionissia A. PepeUniversity College Dublin

Key Points

The aim is to achieve a stereoselective synthesis of glucosides from glycosyl hemiacetals using lithium iodide.
Conducted a one-pot chlorination under Appel conditions.
Applied halide metathesis to convert to iodide with LiI.
Executed a glycosylation sequence with suitable glycosyl acceptors and donors.
Successfully synthesized 1,2-cis-glucosides from glucosyl hemiacetals.
Demonstrated the synthesis of a target pentasaccharide with 4 α-glucosyl linkages.

Abstract

A stereoselective synthesis of 1,2-cis-glucosides from glucosyl hemiacetals is reported herein. It proceeds through a one-pot chlorination (under Appel conditions), halide metathesis to iodide (with LiI), and glycosylation sequence. A range of glycosyl acceptors and donors is shown to be suitable under the reaction conditions. To demonstrate the utility of this method, a target pentasaccharide containing 4 α-glucosyl linkages was synthesized.

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