TY - JOUR
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.
N1 - Publisher Copyright:
Copyright © 2019 American Chemical Society.
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.
UR - http://www.scopus.com/inward/record.url?scp=85069842527&partnerID=8YFLogxK
U2 - 10.1021/acs.orglett.9b01878
DO - 10.1021/acs.orglett.9b01878
M3 - Article
C2 - 31273996
AN - SCOPUS:85069842527
SN - 1523-7060
VL - 21
SP - 5562
EP - 5566
JO - Organic Letters
JF - Organic Letters
IS - 14
ER -