Synthesis of monoglycosides, bisglycosides and open-chain ketoacetals from sugar derived exocyclic enol ethers?

RSC Advances Pub Date: 2014-06-23 DOI: 10.1039/C4RA03340J

Abstract

Under acidic conditions, the reaction of pent-4-enofuranosides with various nucleophiles of mostly alcohol origin furnished bisglycosylated products along with open-chain ketoacetals and monoglycosylated products depending upon the reagents and reaction conditions. The reactions appear to proceed via nucleophilic attack at C-1 and/or C-4 of the reaction intermediates.

Graphical abstract: Synthesis of monoglycosides, bisglycosides and open-chain ketoacetals from sugar derived exocyclic enol ethers
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