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.
J. Y. C. Chan, L. Hough and A. C. Richardson, J. Chem. Soc., Chem. Commun., 1982, 1151 DOI: 10.1039/C39820001151
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