Glycosyl fluoride--A superb glycosyl donor in glycosylation

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  • MUKAIYAMA Teruaki
    The Kitasato Institute, Center for Basic Research
  • JONA Hideki
    The Kitasato Institute, Center for Basic Research Tsukuba Research Institute, Banyu Pharmaceutical Co., Ltd.

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  • Glycosyl fluoride
  • A superb glycosyl donor in glycosylation

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Catalytic and stereoselective glycosylations using glycosyl fluorides are described: 1) activation of armed glycosyl fluorides by trityl tetrakis(pentafluorophenyl)borate [TrB(C6F5)4] catalyst in trifluoromethylbenzene (BTF)-pivalonitrile ('BuCN)(5:1) to afford the corresponding disaccharides in high yields with good to high β-stereoselectivity; 2) activation of disarmed glycosyl fluorides by the combined use of silver tetrakis(pentafluorophenyl)borate [AgB(C6F5)4] and stannous chloride (SnCl2) or stannic chloride<br>(SnCl4); and 3) selective α or β glycosylation using glycosyl fluoride by an appropriate choice of erotic acid catalysts and solvents. Also, the effect of counter anions of erotic acid catalysts on controlling the stereo-selectivities of glycosylation is newly noted. Finally, efficient one-pot sequential syntheses of trisaccharide, F1α antigen, and branched heptasaccharide are demonstrated.

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