Deoxyhalo sugars

It is puzzling that the chlorine and other halogen substituents are not known to enhance the sweetness of other sugars, such as methyl -d-glycopyranosides, a,a-trehalose, maltose, or lactose. On the contrary, all of the deoxyhalo sugar derivatives tasted were extremely bitter. The high sweetness of the deoxyhalosucroses is clearly inexplicable in terms of either... 

Bimolecular, nucleophilic-displacement reactions of sugar sulfonates have been reviewed in this Series.58,59 The value of these reactions in the preparation of deoxyhalo sugars has been emphasized by Hanessian.92... 

Azidodeoxy sugars are useful intermediates in the synthesis of aminodeoxy sugars. Nucleophilic-displacement reactions of sulfonate and deoxyhalo derivatives of sucrose with sodium azide have been used for the preparation of sucrose azides. The reaction of... 

A further use of reagent 39, namely, in the synthesis of deoxyhalo-geno sugars by way of cleavage of oxiranes, is discussed in Section 11,5 (see p. 278). 

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