Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

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

doi:10.1021/acs.orglett.9b01878

Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

Julien A. Delbrouck, Valentin N. Bochatay, Abdellatif Tikad, Stéphane P. Vincent

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	5562-5566
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	14
DOIs	https://doi.org/10.1021/acs.orglett.9b01878
Publication status	Published - 5 Jul 2019

Access to Document

10.1021/acs.orglett.9b01878

Cite this

@article{8f1940e58ea24345a49f183e7b5c84f6,

title = "Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification",

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.}",

note = "Publisher Copyright: Copyright {\textcopyright} 2019 American Chemical Society.",

year = "2019",

month = jul,

day = "5",

doi = "10.1021/acs.orglett.9b01878",

language = "English",

volume = "21",

pages = "5562--5566",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "14",

}

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.

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 -

Regioselective Synthesis of Difluorinated C-Furanosides Involving a Debenzylative Cycloetherification

Abstract

Access to Document

Other files and links

Fingerprint

Cite this