STEREOSELECTIVE SYNTHESIS OF 3-(D-GLYCOPYRANOSYL)PROPENES BY USE OF ALLYLSILANES

Article abstract of DOI:10.1016/S0008-6215(00)90889-9

Reactions of allylsilanes with methyl pyranosides and pyranosyl chlorides proceeded very smoothly in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate and iodosilane to give the corresponding glycopyranosyl-3-propenes in highly stereoselective mode.The configuration depends upon the structure of allylsilanes. 2-Bromo-2-propenyltrimethylsilane, the lowest nucleophile among the allylsilanes used, afforded an almost pure C-α-glycosyl compound.