A facile method for synthesizing selenoglycosides based on selenium-transfer to glycosyl imidate

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 of 2-(trimethylsilyl)ethylselenoglycoside, which, upon treatment with TBAF in the presence of an electrophile, was transformed into other selenoglycosides.