Concepedia

Iodine Monochloride/Silver Trifluoromethanesulfonate (ICl/AgOTf) as a Convenient Promoter System for <i>O</i>-Glycoside Synthesis

Teddy Ercégovic, Andréas Meijer, Göran Magnusson, Ulf Ellervik

Organic Letters · 2001 · 57 citations · 8 references

DOI

Abstract

The novel promoter system iodine monochloride/silver trifluoromethanesulfonate (ICl/AgOTf) was evaluated with various thioglycoside donors and saccharide acceptors, and O-glycosides were obtained in 46-82% yield. Several practical advantages of the ICl/AgOTf system over known promoter systems were observed, such as convenient handling of the reagents and absence of byproducts related to N-succinimide.

References

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Alkyl sulfenyl triflate as activator in the thioglycoside-mediated formation of β-glycosidic linkages during oligosaccharide synthesis

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Stereoselective α-Sialylation with Sialyl Xanthate and Phenylsulfenyl Triflate as a Promotor

Valeri Martichonok, George M. Whitesides · The Journal of Organic Chemistry · 1996 · 146 citations

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Glycosylation with N-Troc-protected glycosyl donors

Ulf Ellervik, Göran Magnusson · Carbohydrate Research · 1996 · 126 citations

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A novel stereoselective synthesis of N-acetyl-α-neuraminosyl-galactose di-saccharide derivatives, using anomeric S-glycosyl xanthates

Alberto Marra, Pierre Sînaÿ · Carbohydrate Research · 1990 · 103 citations

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