Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates

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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.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates ; day:15 ; month:05 ; year:2023 ; extent:12
European journal of organic chemistry ; (15.05.2023) (gesamt 12)

Creator: Ahmadian‐Moghaddam, Maryam
Reintjens, Niels R. M.
Witte, Martin D.
Minnaard, Adriaan Jacobus

DOI: 10.1002/ejoc.202300281

URN: urn:nbn:de:101:1-2023051515315368005247

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

Last update: 14.08.2025, 11:00 AM CEST

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Ahmadian‐Moghaddam, Maryam
Reintjens, Niels R. M.
Witte, Martin D.
Minnaard, Adriaan Jacobus

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Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates

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Other Objects (12)

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