Carbohydrate Research p. 223 - 232 (1987)
Update date:2022-08-03
Topics:
Hosomi, Akira
Sakata, Yasuyuki
Sakurai, Hideki
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.
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