Title: Synthesis of C-furanosides from a<scp>d</scp>-glucal-derived cyclopropane through a ring-expansion/ring-contraction sequence
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.
Publication Year: 2010
Publication Date: 2010-09-20
Language: en
Type: article
Indexed In: ['crossref', 'pubmed']
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Cited By Count: 22
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