Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification | Zendy

Julien A. Delbrouck | Zendy; Valentin N. Bochatay | Zendy; Abdellatif Tikad | Zendy; Stéphane P. Vincent | Zendy

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Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

Author(s) -

Julien A. Delbrouck,

Valentin N. Bochatay,

Abdellatif Tikad,

Stéphane P. Vincent

Publication year - 2019

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.9b01878

Subject(s) - regioselectivity , chemistry , scope (computer science) , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , computer science , programming language

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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