کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1313964 | 1499326 | 2015 | 7 صفحه PDF | دانلود رایگان |
![عکس صفحه اول مقاله: The synthesis of tetrafluorinated aminosugars The synthesis of tetrafluorinated aminosugars](/preview/png/1313964.png)
• 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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Journal: Journal of Fluorine Chemistry - Volume 174, June 2015, Pages 95–101