Halodeoxy sugars

The Preparation of Halodeoxy Sugars by Displacement of Sulfonate Esters... 

Metal halide salts other than sodium iodide have been used sparsely to prepare halodeoxy sugars from sulfonate esters. Lithium chloride (107) and lithium bromide (33) have found limited application. Potassium fluoride (dihydrate) in absolute methanol has been used (51, 52) to introduce fluorine atoms in terminal positions of various D-glucose derivatives. The reaction is conducted in sealed tube systems and requires... 

The synthesis of halodeoxy sugars has also been achieved by reaction of sugar phosphorodiamido and phosphonamido derivatives with alkyl halides (83). Heating equimolar amounts of 6-(tetraethylphosphoro-diamido)-l,2 3,4-di-0 isopropylidene-D-galactose with methyl iodide (and benzyl bromide) at 140°C. for 4 hours afforded the 6-deoxy-6-iodo (74b) (75%) and 6-bromo-6-deoxy (74c) (56%) derivatives, respectively. 

S. Hanessian, Some approaches to the synthesis of halodeoxy sugars, Adv. Chem. Ser. 74 159 (1968). 

Halodeoxy sugars are a class of carbohydrate derivatives in which one or more of the nonanomeric hydroxyl group(s) is substituted with a halogen atom(s). 

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