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A versatile and stereocontrolled route to pyranose and furanose C-glycosides

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JournalOrganic Letters
DatePublished - 22 Jul 2004
Issue number15
Volume6
Number of pages4
Pages (from-to)2611-2614
Original languageEnglish

Abstract

The alpha,beta-unsaturated-gamma,delta-epoxyester 1 is a novel and versatile precursor to a wide variety of C-glycosides. For instance, treatment of Z-1 or E-1 with palladium(0) affords, stereospecifically, beta- or alpha-C-furanosides, respectively. In contrast, reaction of Z-1 or E-1 with base gives, stereoselectively, the beta- or alpha-C-pyranosides, respectively.

    Research areas

  • RAMBERG-BACKLUND APPROACH, LINKED DISACCHARIDES, CYCLIC ETHERS, AMINO-ACIDS, CHEMISTRY, RING, NUCLEOSIDES, TETRAHYDROPYRANS, CONSTRUCTION, CYCLIZATION

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