Fluorodeoxy sugars

A presentation by Webber and co-workers dealing with the synthesis of fluorodeoxy sugars regrettably had to be left out of this monograph because of unexpected difficulties in the preparation of the manuscript. The fourth aspect was represented in the symposium by two presentations involving important aspects of deoxy and dideoxy sugars by Osborn and Heath respectively which unfortunately were not incorporated in this monograph. 

Table 1. F NMR Chemical Shifts for Fluorodeoxy Sugars Free and Complexed to the Receptor ...

The use of tetra-n-butylammonium fluoride (54) in an aprotic solvent such as acetonitrile may be more advantageous. Foster and colleagues (19, 37) have effected an SN2 type of reaction using this reagent in the conversion of l,2 5,6-di-0-isopropylidene-3-0-p-tolylsulfonyl-D-allofura-nose into the C-3 epimeric fluorodeoxy derivative. Note that whereas potassium fluoride is ineffective in displacing secondary sulfonate esters in sugars, tetra-n-butylammonium fluoride is capable of effecting a displacement with Walden inversion even in a furanose drivative. 

Fluorodeoxy glucose compounds and C labeled sugars were purchased through Sigma chemical company. Fluorodeoxy galactose compounds were a generous gift from Dr. Stephen Withers, University of British Columbia. 

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