Add time:07/17/2019 Source:sciencedirect.com
Reaction of propargylaldehyde diethyl acetals 1, 2, 3, and 4 and 2,3,4,6-tetra-O-acetyl-1-O-trimethylsilyl-β-d-glucopyranose 5a in the presence of catalytic amounts of trimethylsilyl trifluoromethanesulfonate at −78°C gives the acetylated acetal-β-glucosides 6–9 in 60–90% yield with retention of configuration at C-1. Likewise 2,3,4,6-tetra-O-acetyl-1-O-trimethylsily-β-d-glucopyranose 5a afforded, after in situ anomerisation to 5b with 4, the corresponding acetal-α-glucoside 10. Hydrogenation and subsequent deprotection yielded the highly acid-sensitive 2-alkenyl-1-ethoxy glucosides which are of interest as selective anticancer agents.
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