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Chemical communications (Cambridge, England)

Synthesis of C-furanosides from a D-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence.


PMID 20852781

Abstract

gem-Dibromocyclopropane 1, prepared from tri-O-benzyl-D-glucal, undergoes thermal and silver-promoted ring expansion in the presence of alcohols to give substituted oxepines. With further heating, ring contraction to highly substituted tetrahydrofurans follows. These represent C-furanosides, potentially useful as precursors to C-nucleosides and other carbohydrate mimics.

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