O-Glycosyl Donors
3.4
613
⊡ Scheme 43
Seeberger’s NPG-based linkers for oligosaccharide synthesis
⊡ Scheme 44
A fluorinated selenide linker for solid-phase synthesis of NPGs
Mogemark et al. described a fluorinated selenide linker 285, for solid-phase synthesis of NPGs
( > Scheme 44) [148]. The resin-bound linker could be glycosylated both with trichloroacetimidates and glycosyl fluorides to give anchored saccharides, e. g. 286, that can be submitted
to glycosylation once deprotected. After oxidation to a selenoxide with t-BuOOH the linker
undergoes β-elimination upon heating, and releases the NPG 287, in excellent yield.
3.4
613
⊡ Scheme 43
Seeberger’s NPG-based linkers for oligosaccharide synthesis
⊡ Scheme 44
A fluorinated selenide linker for solid-phase synthesis of NPGs
Mogemark et al. described a fluorinated selenide linker 285, for solid-phase synthesis of NPGs
( > Scheme 44) [148]. The resin-bound linker could be glycosylated both with trichloroacetimidates and glycosyl fluorides to give anchored saccharides, e. g. 286, that can be submitted
to glycosylation once deprotected. After oxidation to a selenoxide with t-BuOOH the linker
undergoes β-elimination upon heating, and releases the NPG 287, in excellent yield.