A fluorinated selenide linker for solid-phase synthesis of n-pentenyl glycosides.
[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.
Mogemark
Mickael
M
Organic Chemistry, Department of Chemistry, Umeå University, SE-901 87 Umeå, Sweden.
Gustafsson
Linda
L
Bengtsson
Christoffer
C
Elofsson
Mikael
M
Kihlberg
Jan
J
D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D018036:Selenium Compounds / Q000737:chemistry*
D005960:Glucosides; D006845:Hydrocarbons, Fluorinated; D018036:Selenium Compounds