Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

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Abstract: The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting‐group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis‐glucosylations.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity ; volume:57 ; number:27 ; year:2018 ; pages:8240-8244 ; extent:5
Angewandte Chemie / International edition. International edition ; 57, Heft 27 (2018), 8240-8244 (gesamt 5)

Creator: van der Vorm, Stefan
van Hengst, Jacob M. A.
Bakker, Marloes
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Codée, Jeroen D. C.

DOI: 10.1002/anie.201802899

URN: urn:nbn:de:101:1-2022081809004583106252

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2024, 8:28 AM CEST

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Associated

van der Vorm, Stefan
van Hengst, Jacob M. A.
Bakker, Marloes
Overkleeft, Herman S.
van der Marel, Gijsbert A.
Codée, Jeroen D. C.

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