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A facile reaction for constructing selenoglycosides has been developed based on the transacetalization reaction between a selenoacetal and a glycosyl imidate. Glycosyl imidates were activated with TMSOTf to produce oxocarbenium ion, which reacted with benzyloxymethyl alkyl (aryl) selenide, providing alky (or aryl) selenoglycosides in high yields. Furthermore, this reaction was utilized in the synthesis...
The acyl side chain segment 2 contained in polyoxypeptins A (1a) and B (1b), apoptosis-inducing cyclodepsipeptides, was synthesized from chiral 2,3-epoxy alcohol (6), easily prepared by Sharpless asymmetric epoxidation, through a regioselective ring-opening reaction as the key step.
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