The synthesis of 3,4-dideoxy-3,4-difluoro-D-glucose

Clément Q. Fontenelle; Dmitry Shishmarev; Philip W. Kuchel; Bruno Linclau

The synthesis of 3,4-dideoxy-3,4-difluoro-D-glucose

Clément Q. Fontenelle, Dmitry Shishmarev, Philip W. Kuchel, Bruno Linclau^*

^*Corresponding author for this work

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

9 Citations (Scopus)

Abstract

The synthesis of a novel dideoxydifluorinated fluorosugar is described starting from levoglucosan. The fluorine atoms were introduced sequentially through 3,4-epoxide opening and retentive 3-OH deoxofluorination. This latter process was accompanied by a rearrangement process involving the 2-OBn group, which is consistent with previous results of Karban et. al. (Beilst. J. Org. Chem. 2016, 12, 750), who observed a similar rearrangement involving a 2-azido group.

Original language	English
Pages (from-to)	29-34
Number of pages	6
Journal	Trends in Carbohydrate Research
Volume	9
Issue number	1
Publication status	Published - 2017
Externally published	Yes

Cite this

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abstract = "The synthesis of a novel dideoxydifluorinated fluorosugar is described starting from levoglucosan. The fluorine atoms were introduced sequentially through 3,4-epoxide opening and retentive 3-OH deoxofluorination. This latter process was accompanied by a rearrangement process involving the 2-OBn group, which is consistent with previous results of Karban et. al. (Beilst. J. Org. Chem. 2016, 12, 750), who observed a similar rearrangement involving a 2-azido group.",

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T1 - The synthesis of 3,4-dideoxy-3,4-difluoro-D-glucose

AU - Fontenelle, Clément Q.

AU - Shishmarev, Dmitry

AU - Kuchel, Philip W.

AU - Linclau, Bruno

PY - 2017

Y1 - 2017

N2 - The synthesis of a novel dideoxydifluorinated fluorosugar is described starting from levoglucosan. The fluorine atoms were introduced sequentially through 3,4-epoxide opening and retentive 3-OH deoxofluorination. This latter process was accompanied by a rearrangement process involving the 2-OBn group, which is consistent with previous results of Karban et. al. (Beilst. J. Org. Chem. 2016, 12, 750), who observed a similar rearrangement involving a 2-azido group.

AB - The synthesis of a novel dideoxydifluorinated fluorosugar is described starting from levoglucosan. The fluorine atoms were introduced sequentially through 3,4-epoxide opening and retentive 3-OH deoxofluorination. This latter process was accompanied by a rearrangement process involving the 2-OBn group, which is consistent with previous results of Karban et. al. (Beilst. J. Org. Chem. 2016, 12, 750), who observed a similar rearrangement involving a 2-azido group.

KW - Dideoxy sugar

KW - Fluorosugar

KW - Levoglucosan

KW - Rearrangement

KW - Retentive fluorination

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M3 - Article

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JO - Trends in Carbohydrate Research

JF - Trends in Carbohydrate Research

IS - 1

ER -

The synthesis of 3,4-dideoxy-3,4-difluoro-D-glucose

Abstract

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