Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1313964 | Journal of Fluorine Chemistry | 2015 | 7 Pages |
•The synthesis of two novel fluorinated aminosugars is described.•Key step involves addition of lithiated 1-bromo-1,1,2,2-tetrafluorobutene.•High stereoselectivity was obtained with sulfinylimines.•Both sulfinylimine diastereomers derived from d-glyceraldehyde were used.
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 α-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.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide