Protic acid catalyzed stereoselective glycosylation using glycosyl fluorides

Hideki Jona, Hiroki Mandai, Warinthorn Chavasiri, Kazuya Takeuchi, Teruaki Mukaiyama

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

A catalytic and stereoselective glycosylation of various glycosyl acceptors, such as methyl glycosides, thioglycosides, or a disarmed glycosyl fluoride, with benzyl-protected armed glycosyl fluoride was successfully carried out by using various protic acids in the presence of MS 5A. In the cases when trifluoromethanesulfonic acid (TfOH) or perchloric acid (HClO4) was used in diethyl ether (Et2O), α-glycosides were obtained as major products, 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. Stereoselectivity of this glycosylation was controlled by the properties of counter anions of the catalyst as well as by those of solvents. Also, one-pot trisaccharide synthesis was performed by successive addition of NIS and third-sugar to afford Glcα or β1-6Glcβ1-6Glc and Glcα or β1-6GlcNβ1-6Glc in excellent yields.

Original languageEnglish
Pages (from-to)291-309
Number of pages19
JournalBulletin of the Chemical Society of Japan
Volume75
Issue number2
DOIs
Publication statusPublished - Mar 14 2002

ASJC Scopus subject areas

  • Chemistry(all)

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