Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

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Abstract

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.

Original languageEnglish
Pages (from-to)5562-5566
Number of pages5
JournalOrganic Letters
Volume21
Issue number14
DOIs
Publication statusPublished - 5 Jul 2019

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Gems
Pentoses
Hexoses
pentose
hexoses
synthesis
diethylaminosulfur trifluoride

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abstract = "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.",
author = "Delbrouck, {Julien A.} and Bochatay, {Valentin N.} and Abdellatif Tikad and Vincent, {St{\'e}phane P.}",
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T1 - Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

AU - Delbrouck, Julien A.

AU - Bochatay, Valentin N.

AU - Tikad, Abdellatif

AU - Vincent, Stéphane P.

PY - 2019/7/5

Y1 - 2019/7/5

N2 - 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.

AB - 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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