The synthesis of tetrafluorinated aminosugars
The synthesis of tetrafluorinated aminosugars
The synthesis of two tetrafluorinated 4-aminosugars, 4-amino-2,3,4-trideoxy-2,2,3,3-tetrafluoro-d-erythro-hexopyranose hydrochloride (7•HCl) and 4-amino-2,3,4-trideoxy-2,2,3,3-tetrafluoro-d-threo-hexopyranose hydrochloride (8•HCl), is described. The amino group in ?-position of a CF2(CF2) group is proposed as a mimic for the hydrogen bond accepting capacity of an alcohol group in an unfluorinated sugar. The synthesis of the two sugars was achieved in 4 steps each from the sulfinylimine diastereoisomers of d-glyceraldehyde.
fluorine, carbohydrate, fluorosugar, fluorination, aminosugar
Fontenelle, Clément Q.
c746c5ea-96bc-46c2-849d-47215ab58c03
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
28 July 2014
Fontenelle, Clément Q.
c746c5ea-96bc-46c2-849d-47215ab58c03
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Linclau, Bruno
19b9cacd-b8e8-4c65-af36-6352cade84ba
Fontenelle, Clément Q., Tizzard, Graham J. and Linclau, Bruno
(2014)
The synthesis of tetrafluorinated aminosugars.
Journal of Fluorine Chemistry.
(doi:10.1016/j.jfluchem.2014.07.015).
Abstract
The synthesis of two tetrafluorinated 4-aminosugars, 4-amino-2,3,4-trideoxy-2,2,3,3-tetrafluoro-d-erythro-hexopyranose hydrochloride (7•HCl) and 4-amino-2,3,4-trideoxy-2,2,3,3-tetrafluoro-d-threo-hexopyranose hydrochloride (8•HCl), is described. The amino group in ?-position of a CF2(CF2) group is proposed as a mimic for the hydrogen bond accepting capacity of an alcohol group in an unfluorinated sugar. The synthesis of the two sugars was achieved in 4 steps each from the sulfinylimine diastereoisomers of d-glyceraldehyde.
Text
Linclau revised manuscript_eprints.pdf
- Accepted Manuscript
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Published date: 28 July 2014
Keywords:
fluorine, carbohydrate, fluorosugar, fluorination, aminosugar
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Local EPrints ID: 373314
URI: http://eprints.soton.ac.uk/id/eprint/373314
ISSN: 0022-1139
PURE UUID: a3084dca-8f46-4b57-b108-91606d303e36
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Date deposited: 14 Jan 2015 17:14
Last modified: 15 Mar 2024 03:10
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Author:
Clément Q. Fontenelle
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