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

Hideki Jona; Hiroki Mandai; Teruaki Mukaiyama

doi:10.1246/cl.2001.426

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

Hideki Jona, Hiroki Mandai, Teruaki Mukaiyama

Graduate School of Natural Science and Technology

Research output: Contribution to journal › Article › peer-review

40 Citations (Scopus)

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 language	English
Pages (from-to)	426-427
Number of pages	2
Journal	Chemistry Letters
Issue number	5
DOIs	https://doi.org/10.1246/cl.2001.426
Publication status	Published - Jan 1 2001

ASJC Scopus subject areas

Chemistry(all)

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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-.",

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AB - 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-.

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

Abstract

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