A catalytic and stereoselective glycosylation with glucopyranosyl fluoride by using various protic acids

Hideki Jona, Hiroki Mandai, Teruaki Mukaiyama

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Abstract

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-.

Original languageEnglish
Pages (from-to)426-427
Number of pages2
JournalChemistry Letters
Issue number5
DOIs
Publication statusPublished - Jan 1 2001

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ASJC Scopus subject areas

  • Chemistry(all)

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