Polymer-bound diphenylphosphane hydrobromide, a mild acid for the activation of enol ethers: Applications in polymer-assisted glycosidations

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OriginalspracheEnglisch
Seiten (von - bis)3435-3446
Seitenumfang12
FachzeitschriftEuropean Journal of Organic Chemistry
Ausgabenummer16
PublikationsstatusVeröffentlicht - 3 Aug. 2004

Abstract

Polymer-bound diphenylphosphane hydrobromide 2 shows excellent properties in the activation of enol ethers and glycals, the introduction and cleavage of THP ethers being promoted with excellent yields with this functionalized polymer, Glycosidations of glycals work equally well, with suppression of the formation of undesired Ferrier rearranged products. The reagent is sufficiently mild to leave labile 2-deoxy glycosidic bonds and acid-labile protecting groups intact. It can be employed to transfer disaccharide glycosyl donors onto aglycons and is also selective for the promotion of two glycosidations in one pot, Highly hindered glycosyl donor groups such as the hydroxy group at C-13 of the baccatin III framework can be glycosylated with glycals in the presence of this polymer-bound reagent.

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Polymer-bound diphenylphosphane hydrobromide, a mild acid for the activation of enol ethers: Applications in polymer-assisted glycosidations. / Jaunzems, Janis; Kashin, Dmitri; Schönberger, Andreas et al.
in: European Journal of Organic Chemistry, Nr. 16, 03.08.2004, S. 3435-3446.

Publikation: Beitrag in FachzeitschriftArtikelForschungPeer-Review

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T1 - Polymer-bound diphenylphosphane hydrobromide, a mild acid for the activation of enol ethers

T2 - Applications in polymer-assisted glycosidations

AU - Jaunzems, Janis

AU - Kashin, Dmitri

AU - Schönberger, Andreas

AU - Kirschning, Andreas

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KW - Glycoconjugates

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KW - Multistep synthesis

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