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Applications of Thioglycosides

The application of thioglycoside gained a new impetus by the finding of Kahne et al. [56] who observed that phenylsulfenyl glycosyl donors, readily accessible by oxidation (/mCPBA) of phenyl thioglycosides, can be effectively glycosylated using... [Pg.82]

The application of diazo coupling is somewhat limited by the availability of the p-aminophenyl glycosides, particularly of those of the oligosaccharides. Their precursors, the p-nitrophenyl glycosides, are usually obtained by the condensation of a per-O-acetylated glycosyl halide with p-nitrophenol in ethanol (Michael reaction)19,20 or by the reaction of a per-O-acetylated sugar with p-nitrophenol in the presence of a Lewis acid catalyst (Helferich reaction).21 p-Nitrobenzyl 1-thioglycosides have also been prepared by the condensation of the... [Pg.230]

Takeuchi, K, Tamura, T, Mukaiyama, T, Stereoselective glycosylation of thioglycosides promoted by respective combinations of A-iodo- or A-bromosuccinimide and trityl tetrakisfpentafluorophe-nyl)borate. Application to one-pot sequential synthesis of trisaccharide. Tetrahedron Lett., 124-125, 2000. [Pg.179]

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1-Thioglycosides

Thioglycoside

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