Catalytic glycosylation with designer thioglycoside and novel protecting groups for same and for synthesis of oligosaccharides

摘要

A catalytic glycosylation method comprising: installing thioether to an anomeric carbon of a carbohydrate; and catalytically activating the thioether with a non-oxophilic Lewis acid. The thioether may comprise an anomerically stable thioether leaving group. The catalytic glycosylation method may further comprise: utilizing an acid-sensitive ester protecting group as permanent protecting group or using a reactivity-based one-pot glycosylation that employs a single-component catalyst to accelerate an oligosaccharide assembly process. A protecting group to mask hydroxyl functionalities in the production of oligosaccharides, natural products or any molecule having a hydroxyl group comprising an acid-labile ester protecting group.

主权项

1. A catalytic glycosylation method comprising: installing an anomerically-stable thioether leaving group onto an anomeric carbon of a carbohydrate to yield an ortho-alkynylphenyl thioglycoside, wherein the anomerically stable thioether leaving group is ortho-alkynylthiophenol; and catalytically activating the anomerically-stable thioether leaving group with an activator comprising PPh3AuNTf2.