The synthesis of tetrafluorinated aminosugars

• 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.

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