Enantioselective synthesis of tetrafluorinated glucose and galactose.
Polyfluorinated carbohydrates have emerged as interesting probes to investigate "polar hydrophobicity" effect(s) in protein-carbohydrate interactions. A convenient enantioselective synthesis of tetrafluorinated analogues of two of the most important monosaccharides, D-glucose and D-galactose, is reported, as well as our first results regarding the glycosylation of these sugar analogues.
Timofte
Roxana S
RS
University of Southampton, School of Chemistry, Highfield, Southampton SO17 1BJ.
Linclau
Bruno
B
D003500:Cyclization; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D005947:Glucose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D006031:Glycosylation; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis; D013237:Stereoisomerism
D006845:Hydrocarbons, Fluorinated; D005947:Glucose; D005690:Galactose