Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates
Abstract: A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C‐3 hydroxy group in gluco‐configured pyranosides, followed by stereoselective indium‐mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene‐tetrahydrofuran‐containing carbohydrates.
- Standort
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Deutsche Nationalbibliothek Frankfurt am Main
- Umfang
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Online-Ressource
- Sprache
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Englisch
- Erschienen in
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Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates ; day:15 ; month:05 ; year:2023 ; extent:12
European journal of organic chemistry ; (15.05.2023) (gesamt 12)
- Urheber
- DOI
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10.1002/ejoc.202300281
- URN
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urn:nbn:de:101:1-2023051515315368005247
- Rechteinformation
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Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
- Letzte Aktualisierung
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14.08.2025, 11:00 MESZ
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Beteiligte
- Ahmadian‐Moghaddam, Maryam
- Reintjens, Niels R. M.
- Witte, Martin D.
- Minnaard, Adriaan Jacobus
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