What is the reaction mechanism between HF-pyridine( Olah reagent) and carbohydrates (xylose,glucose)?

03 April 2016 1 2K Report

Hello,

Does anyone know the mechanism of synthesis of glycosyl fluorides?

I am looking for the mechanism of synthesis of alpha-D-xylopyranosyl fluoride from HF-pyridine( Olah reagent) and 1,2,3,4-Tetra-O-acetyl-b-D-xylopyranose.

Thanks,

Oleg

Johann Heider

superacid protonates oxygen of C1 (either OH or OR group), water or alcohol is eliminated leaving a glycosyl cation, which adds fluoride.

see Martin et al. 2016 Nature Chemistry 8:186

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