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Regioselective Synthesis of Difluorinated C‑Furanosides Involving a Debenzylative Cycloetherification

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journal contribution
posted on 05.07.2019, 00:00 by Julien A. Delbrouck, Valentin N. Bochatay, Abdellatif Tikad, Stéphane P. Vincent
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.