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Syntheses of (R)-1,4,7,10-tetraoxaspiro[5.5]undecane (spirobi-1,4-dioxan), (R)-1,4,7-trioxa-10-thiaspiro[5.5]undecane, and (R)-1,4,7-trioxa-10-azaspiro[5.5]undecane from 2′-chloroethyl β-D-fructopyranoside are reported, in which the chirality of the spiro-ring junction is defined by the configuration of the anomeric carbon atom of the glycoside.


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