Co-host: The Chemical Society of Japan, The Society of Synthetic Organic Chemistry, Japan (Cooperation)
The reaction of 2,3,4,6-tetra-O-benzyl-1-C-vinyl-D-glucopyranose with several nucleophiles in the presence of Lewis acids was investigated. When allyltrimethylsilane and silyl enol ethers were used as the nucleophiles, we found that the reaction conditions using 20 mol% TMSOTf promoted the SN1' reaction to afford the corresponding exo-(Z)-glycals, which was caused by the attack of the nucleophiles to the terminal olefinic carbon atom in the glycosyl cation intermediate.
