A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides
Mickael Mogemark1, Linda Gustafsson, Christoffer Bengtsson
1Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden.
Organic Letters
|December 21, 2004
Abstract:
[reaction: see text] A fluorine-labeled selenide linker for installing terminal isolated olefins has been synthesized in high overall yield. The resin-bound linker could be glycosylated both with glycosyl trichloroacetimidates and glycosyl fluorides. The linker did not decompose after oxidation with tBuOOH but underwent beta-elimination when it was subjected to heat. This allowed the released n-pentenyl glycoside 15 to be isolated in excellent yield and purity after filtration.


