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[摘要]：A modular and efficient synthesis of 5-(hetero)arylfuran C-2'-deoxyribonucleosides was developed Friedel Crafts glycosidation of 2-bromofuran with toluoyl-protected methyl 2'-deoxyribofuranoside in the presence of BF3 center dot Et2O gave 5-bromofuran C-nucleosides, which were used as key intermediates for Stille or Suzuki coupling with (hetero)arylstannanes or boronic acids to afford a series of 5-(hetero)arylfuran C-nucleosides. 5-Boronofuran C-nucleoside was prepared by the Suzuki coupling of bromofuran with bis(pinacolatodiboron) or by Ir-catalyzed C-H borylation of furan and was used for cross-coupling with 5-bromoheteroaryl C-nucleosides to furnish novel covalent analogues of nucleoside pairs The title 5-arylfuran C-nucleosides possess interesting fluorescence properties that may be applicable for fluorescent labeling of biomolecules |
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