Complex tetrahydrofurans from carbohydrate lactones: easy access to epimeric C-glycosides of glucofuranose from D-glycero-D-gulo-heptono-1,4-lactone

Abstract

A practical synthesis of epimeric C-glycosides of glucofuranose from the cheap gluco-heptono-1,4-lactone is reported; the ring contractions of 2-O-triflates of protected gluco-heptono-1,5-lactones are discussed. No tetrahydropyrancarboxylates were isolated from any of the reactions.