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Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions

Abstract : Substitution of the participating group of glycosyl donors by a halogen atom is shown to specifically induce degradation of transient orthoesters formed during glycosylation reactions, depending on the nature of the acceptor, and to affect the protonation profile of those intermediates. Following these findings, bromo- and chloroacetates, which are major protecting groups in glycochemistry because they are orthogonal to other esters, should be considered with care as participating groups in the future.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02046285
Contributor : Madeleine Roux-Merlin <>
Submitted on : Friday, February 22, 2019 - 3:39:55 PM
Last modification on : Saturday, September 19, 2020 - 3:44:22 AM

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Antoine Joosten, Mélissa Boultadakis-Arapinis, V. Gandon, L. Micouin, Thomas Lecourt. Substitution of the Participating Group of Glycosyl Donors by a Halogen Atom: Influence on the Rearrangement of Transient Orthoesters Formed during Glycosylation Reactions. Journal of Organic Chemistry, American Chemical Society, 2017, 82 (6), pp.3291-3297. ⟨10.1021/acs.joc.6b03088⟩. ⟨hal-02046285⟩

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