Abstract
The treatment of C-1 gem dihalogenosugars with silver triflate or mercury cyanide in the presence of simple alcohols α or ω diols or catechol constitutes a general method of orthoesterification. Depending on the structure of the nucleophile the anomeric carbon substitutions can be achieved regioselectively either by intra or intermolecular routes to yield a large variety of anomeric orthoesters including spiranic structures or chiral crown-ethers.The use of a less reactive chiral α-diol [12-O-[l-methylethylidene]-3-O-methyl-α -D-glucofuranose]including primary and secondary hydroxy groups results in a less regioselective transformation. The known reactivity of this diol together with the structure and the distribution of the isolated products support a mecanism which suggests a stereoselective α-cyclization of anomeric dioxacarbenium intermediates.
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