A catalytic and stereoselective glycosylation with glucosyl fluoride was effectively performed by using a catalytic amount of various protic acids. When the glycosylation was carried out, for example, using perchloric acid (HClO4) in diethyl ether (Et2O), the major products were α-glycosides while β-stereoselectivity was observed when tetrakis(pentafluorophenyl)boric acid [HB(C6F5)4] was used in a mixed solvent of trifluoromethylbenzene (BTF)-pivalonitrile (tBuCN) = (5:1). The stereoselectivity was controlled by not only the effect of solvent but also by the nature of counter anion of the catalyst such as B(C6F5)4- or ClO4-.
|Number of pages||2|
|Publication status||Published - Jan 1 2001|
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