Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification.
Julien A DelbrouckValentin N BochatayAbdellatif TikadStéphane P VincentPublished in: Organic letters (2019)
A highly regioselective synthesis of valuable gem-difluorinated C-furanosides from unprotected aldoses via a debenzylative cycloetherification (DBCE) reaction induced by diethylaminosulfur trifluoride is descibed. The scope and limitations of this DBCE reaction are described using a series of commercially available pentoses and hexoses to afford, without selective protection/deprotection sequences, the corresponding gem-difluorinated C-furanosides in moderate to good yields.
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