Abstract
Various sugars were C-glycosylated by treatment with methylenetriphenyl-phosphorane and subsequent iodocyclization of the resulting hept- and hex-enitols. In all cases, a Cglycofuranosyl compound was obtained, except for 3,4,5,7-tetra- O-benzyl-1,2-dideoxy- d- manno-hept-1-enitol which yielded a C-pyranosyl compound. High stereoselectoin, with formation of the 1,2- cis adduct as major product, was observed when an asymmetric center was present in the position adjacent to the double bond.
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