| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5262378 | Tetrahedron Letters | 2014 | 4 Pages |
Abstract
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.
Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Tatsuya Suzuki, Naoko Komura, Akihiro Imamura, Hiromune Ando, Hideharu Ishida, Makoto Kiso,