Cyclohexaamylose 6-deoxy-, preparation

Melton and Slessor207 have prepared mono-6-chloro-6-deoxy-, mono-6-bromo-6-deoxy-, and mono-6-deoxy-6-iodo-cyclohexaamylose by nucleophilic displacements of the sulfonate group in mono-6-O-p-tolylsulfonylcyclohexaamylose. The monoiodo and monochloro derivatives were each reduced to mono-6-deoxycyclohexaamylose over W-2 and W-4 Raney nickel catalysts, respectively. 

The preparation of monosubstituted cycloamyloses has also been achieved, and depends primarily on the isolation of 6-O-p-tolylsulfonyl-cyclohexaamylose from the products of short-term p-toluenesulfonylation of cyclohexaamylose. By appropriate, nucleophilic displacements, this compound may be converted into the 6-azido-6-deoxy, 6-bromo-6-deoxy, 6-chloro-6-deoxy, and 6-deoxy-6-iodo derivatives reduction of the azide and iodide gives 6-amino-6-deoxy- and 6-deoxy-cyclohexaamylose, respectively. The preparation of monoesters, namely, cyclohexaamylose monobenzoate, cyclohexaamylose 2,5-pyridinedicarboxylate, and... 

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