Synthesis of Methylene Tetrahydrofurane-Fused Carbohydrates

Maryam Ahmadian-Moghaddam, Niels R.M. Reintjens, Martin D. Witte*, Adriaan J. Minnaard*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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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.

Original languageEnglish
Article numbere202300281
Number of pages11
JournalEuropean Journal of Organic Chemistry
Issue number20
Publication statusPublished - 22-May-2023


  • carbohydrates
  • enol ether
  • iodocyclization
  • photoclick
  • site selectivity

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