Application of the versatile character of the tellurium atom for the synthesis of C-nucleoside analogues via sugar tellurides

Abstract

Making use of the versatile character of the tellurium atom such as its radicophilicity, nucleophilicity and electrophilicity, D-ribofuranosyl, 2-deoxy-D-ribofuranosyl and D-glucosyl p-methoxyphenyl tellurides have been prepared. Under suitable conditions, the corresponding anomeric radical, anomeric cation and anomeric anion, respectively, are formed from the sugar tellurides. By the following coupling reactions of the anomeric radical and anomeric cation to electron-poor and electron-rich aromatics, respectively, the corresponding C-nucleoside analogues have been synthesized in moderate yields. The anomeric anion has also been trapped by an electrophile such as benzaldehyde.