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

Oana G. Popa; Imlirenla Pongener; Dionissia A. Pepe; Chennaiah Ande; Eoghan M. McGarrigle

doi:10.1021/acs.joc.5c02828

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

The Journal of Organic Chemistry 2026

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Authors: Oana G. Popa, Imlirenla Pongener, Dionissia A. Pepe, Chennaiah Ande, Eoghan M. McGarrigle

DOI: 10.1021/acs.joc.5c02828

Cited by: 0

References: 58

Abstract

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.

Fields of Study & Subjects

Carbohydrate Chemistry and Synthesis Glycosylation and Glycoproteins Research Organic Chemistry Synthesis Methods

Publication details

Journal / source: The Journal of Organic Chemistry
Volume: 91
Issue: 7
Pages: 2798–2805
Publication date: 6 February 2026
Language: EN

References 58