Facile One-Pot Synthesis of Resorcinol Bis-C-Glycosides Possessing Two Identical­ Sugar Moieties

Abstract

Two identical C-glycoside moieties were efficiently installed­ in non-protected resorcinol derivatives by the Sc(OTf)₃-catalyzed one-pot procedure.

Key words

bis-C-glycoside - rearrangement reactions - resorcinol - scandium(III) triflate - pluramycin

References

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7

Another possible explanation is that bis-O-glycoside 5, once formed immediately rearranges to mono-O-mono-C-glycoside 7. However, this is unlikely since it was previously shown that protection of one hydroxyl group of a resorcinol derivative remarkably retards the O→C-glycoside rearrangement at the other hydroxyl; see ref. 4.